New strategies in carbonylation chemistry: The synthesis of δ-lactones from saturated alcohols and CO

Journal of the American Chemical Society

Volumn 120, Issue 34, 1998, Pages 8692-8701

  Tsunoi, Shinji ^a   Ryu, Ilhyong ^a   Okuda, Tohru ^a   Tanaka, Minoru ^a   Komatsu, Mitsuo ^a   Sonoda, Noboru ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKANE; CARBON MONOXIDE; LACTONE DERIVATIVE; RADICAL;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; MOLECULAR DYNAMICS; OXIDATION; PROTON TRANSPORT; SYNTHESIS;

EID: 0032475422     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9807892     Document Type: Article

References (174)

1. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
2. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
3. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
4. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
5. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
6. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
7. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
8. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
9. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
10. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
11. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
12. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
13. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
14. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
15. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
16. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
17. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
18. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
19. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (s) Hill, C. L. Synlett 1995, 127. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
20. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
21. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591.
22. For leading references for carbonylation of alkanes, see: (a) Sakakura, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1987, 758. (b) Fujiwara, Y.; Takaki, K.; Watanabe, J.; Uchida, Y.; Taniguchi, H. Chem. Lett. 1989, 1687. (c) Sakakura, T.; Sodeyama, T.; Sasaki, K.; Wada, K.; Tanaka, M. J. Am. Chem. Soc. 1990, 112, 7221. (d) Nakata, K.; Watanabe, J.; Takaki, K.; Fujiwara, Y. Chem. Lett. 1991, 1437. (e) Ferguson, R. R.; Crabtree, R. H. J. Org. Chem. 1991, 56, 5503. (f) Boese, W. T.; Goldman, A. S. J. Am. Chem. Soc. 1992, 114, 350. (g) Sen, A.; Lin, M. J. Chem. Soc., Chem. Commun. 1992, 508. (h) Lin, M.; Sen, A. J. Chem. Soc., Chem. Commun. 1992, 892. (i) Boese, W. T.; Goldman A. S. Tetrahedron Lett. 1992, 33, 2119. (j) Barton, D. H. R.; Csuhai, E.; Doller, D. Tetrahedron Lett. 1992, 33, 4389. (k) Nakata, K.; Yamaoka, Y.; Miyata, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. J. Organomet. Chem. 1994, 473, 329. (l) Lin, M.; Sen, A. Nature 1994, 368, 613. (m) Jaynes, B. S.; Hill, C. L. J. Am. Chem. Soc. 1995, 117, 4704. (n) Barton, D. H. R.; Beck, A. H.; Delanghe, N. C. Tetrahedron Lett. 1996, 37, 1555. (o) Sakakura, T.; Ishiguro, K.; Okano, M.; Sako, T. Chem. Lett. 1997, 1089. (p) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. For reviews on C-H activation chemistry, see: (q) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (r) Barton, D. H. R.; Doller, D. Acc. Chem. Res. 1992, 25, 504. (s) Hill, C. L. Synlett 1995, 127. (t) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res 1995, 28, 154. (u) Fujiwara, Y.; Takaki, K.; Taniguchi, H. Synlett 1996, 591. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879. (v) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879. (b) Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095. Theoretical studies on 1,5-H shift from C to O•, see: (c) Houk, K. N.; Tucker, J. A.; Dorigo, A. E. Acc. Chem. Res. 1990, 23, 107.
23. For reviews on remote functionalization by 1,5-H shift from C to O•, see: (a) Brun, P.; Waegell, B. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1983; Vol. 3, Chapter 6. Theoretical studies on 1,5-H shift from C to O•, see: (c) Houk, K. N.; Tucker, J. A.; Dorigo, A. E. Acc. Chem. Res. 1990, 23, 107.
24. (2) For reviews on remote functionalization by 1,5-H shift from C to O•, see: (a) Brun, P.; Waegell, B. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1983; Vol. 3, Chapter 6. (b) Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095. (b) Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095.
25. (2) For reviews on remote functionalization by 1,5-H shift from C to O•, see: (a) Brun, P.; Waegell, B. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1983; Vol. 3, Chapter 6. (b) Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095. Theoretical studies on 1,5-H shift from C to O•, see: (c) Houk, K. N.; Tucker, J. A.; Dorigo, A. E. Acc. Chem. Res. 1990, 23, 107. Theoretical studies on 1,5-H shift from C to O•, see: (c) Houk, K. N.; Tucker, J. A.; Dorigo, A. E. Acc. Chem. Res. 1990, 23, 107. (b) Barton, D. H. R.; Beaton, J. M. J. Am. Chem. Soc. 1961, 83, 4083. (c) Akhtar, M.; Barton, D. H. R.; Sammes, P. G. J. Am. Chem. Soc. 1965, 87, 4601. (d) Čeković, Ž.; Srnić, T. Tetrahedron Lett. 1976, 561. Also see a review: (e) Barton, D. H. R. Pure Appl. Chem. 1968, 16, 1.
26. For examples of 1,5-H shift from C to O• by the photolysis of nitrite esters, see: (a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1961, 83, 4076. (c) Akhtar, M.; Barton, D. H. R.; Sammes, P. G. J. Am. Chem. Soc. 1965, 87, 4601. (d) Čeković, Ž.; Srnić, T. Tetrahedron Lett. 1976, 561. Also see a review: (e) Barton, D. H. R. Pure Appl. Chem. 1968, 16, 1.
27. For examples of 1,5-H shift from C to O• by the photolysis of nitrite esters, see: (a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1961, 83, 4076. (b) Barton, D. H. R.; Beaton, J. M. J. Am. Chem. Soc. 1961, 83, 4083. (b) Barton, D. H. R.; Beaton, J. M. J. Am. Chem. Soc. 1961, 83, 4083. (d) Čeković, Ž.; Srnić, T. Tetrahedron Lett. 1976, 561. Also see a review: (e) Barton, D. H. R. Pure Appl. Chem. 1968, 16, 1.
28. For examples of 1,5-H shift from C to O• by the photolysis of nitrite esters, see: (a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1961, 83, 4076. (b) Barton, D. H. R.; Beaton, J. M. J. Am. Chem. Soc. 1961, 83, 4083. (c) Akhtar, M.; Barton, D. H. R.; Sammes, P. G. J. Am. Chem. Soc. 1965, 87, 4601. (c) Akhtar, M.; Barton, D. H. R.; Sammes, P. G. J. Am. Chem. Soc. 1965, 87, 4601. Also see a review: (e) Barton, D. H. R. Pure Appl. Chem. 1968, 16, 1.
29. For examples of 1,5-H shift from C to O• by the photolysis of nitrite esters, see: (a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1961, 83, 4076. (b) Barton, D. H. R.; Beaton, J. M. J. Am. Chem. Soc. 1961, 83, 4083. (c) Akhtar, M.; Barton, D. H. R.; Sammes, P. G. J. Am. Chem. Soc. 1965, 87, 4601. (d) Čeković, Ž.; Srnić, T. Tetrahedron Lett. 1976, 561. (d) Čeković, Ž.; Srnić, T. Tetrahedron Lett. 1976, 561.
30. For examples of 1,5-H shift from C to O• by the photolysis of nitrite esters, see: (a) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M. M. J. Am. Chem. Soc. 1961, 83, 4076. (b) Barton, D. H. R.; Beaton, J. M. J. Am. Chem. Soc. 1961, 83, 4083. (c) Akhtar, M.; Barton, D. H. R.; Sammes, P. G. J. Am. Chem. Soc. 1965, 87, 4601. (d) Čeković, Ž.; Srnić, T. Tetrahedron Lett. 1976, 561. Also see a review: (e) Barton, D. H. R. Pure Appl. Chem. 1968, 16, 1. Also see a review: (e) Barton, D. H. R. Pure Appl. Chem. 1968, 16, 1. (b) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1961, 83, 2207. (c) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1961, 83, 2214. (d) Mill, J. S.; Petrov, V. Chem. Ind. 1961, 946. (e) Greene, F. D.; Savitz, M. L.; Osterholtz, F. D.; Lau, H. H.; Smith, W. N.; Zanet, P. M. J. Org. Chem. 1963, 28, 55. (f) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1963, 85, 1597. Also see a review: (g) Walling, C. Pure Appl. Chem. 1967, 15, 69.
31. For examples of 1,5-H shift from C to O• by the photolysis of hypochlorites, see: (a) Greene, F. D.; Savitz, M. L.; Lau, H. H.; Osterholtz, F. D.; Smith, W. N. J. Am. Chem. Soc. 1961, 83, 2196. (c) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1961, 83, 2214. (d) Mill, J. S.; Petrov, V. Chem. Ind. 1961, 946. (e) Greene, F. D.; Savitz, M. L.; Osterholtz, F. D.; Lau, H. H.; Smith, W. N.; Zanet, P. M. J. Org. Chem. 1963, 28, 55. (f) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1963, 85, 1597. Also see a review: (g) Walling, C. Pure Appl. Chem. 1967, 15, 69.
32. (4) For examples of 1,5-H shift from C to O• by the photolysis of hypochlorites, see: (a) Greene, F. D.; Savitz, M. L.; Lau, H. H.; Osterholtz, F. D.; Smith, W. N. J. Am. Chem. Soc. 1961, 83, 2196. (b) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1961, 83, 2207. (b) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1961, 83, 2207. (d) Mill, J. S.; Petrov, V. Chem. Ind. 1961, 946. (e) Greene, F. D.; Savitz, M. L.; Osterholtz, F. D.; Lau, H. H.; Smith, W. N.; Zanet, P. M. J. Org. Chem. 1963, 28, 55. (f) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1963, 85, 1597. Also see a review: (g) Walling, C. Pure Appl. Chem. 1967, 15, 69.
33. (4) For examples of 1,5-H shift from C to O• by the photolysis of hypochlorites, see: (a) Greene, F. D.; Savitz, M. L.; Lau, H. H.; Osterholtz, F. D.; Smith, W. N. J. Am. Chem. Soc. 1961, 83, 2196. (b) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1961, 83, 2207. (c) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1961, 83, 2214. (c) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1961, 83, 2214. (e) Greene, F. D.; Savitz, M. L.; Osterholtz, F. D.; Lau, H. H.; Smith, W. N.; Zanet, P. M. J. Org. Chem. 1963, 28, 55. (f) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1963, 85, 1597. Also see a review: (g) Walling, C. Pure Appl. Chem. 1967, 15, 69.
34. (4) For examples of 1,5-H shift from C to O• by the photolysis of hypochlorites, see: (a) Greene, F. D.; Savitz, M. L.; Lau, H. H.; Osterholtz, F. D.; Smith, W. N. J. Am. Chem. Soc. 1961, 83, 2196. (b) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1961, 83, 2207. (c) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1961, 83, 2214. (d) Mill, J. S.; Petrov, V. Chem. Ind. 1961, 946. (d) Mill, J. S.; Petrov, V. Chem. Ind. 1961, 946. (f) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1963, 85, 1597. Also see a review: (g) Walling, C. Pure Appl. Chem. 1967, 15, 69.
35. (4) For examples of 1,5-H shift from C to O• by the photolysis of hypochlorites, see: (a) Greene, F. D.; Savitz, M. L.; Lau, H. H.; Osterholtz, F. D.; Smith, W. N. J. Am. Chem. Soc. 1961, 83, 2196. (b) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1961, 83, 2207. (c) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1961, 83, 2214. (d) Mill, J. S.; Petrov, V. Chem. Ind. 1961, 946. (e) Greene, F. D.; Savitz, M. L.; Osterholtz, F. D.; Lau, H. H.; Smith, W. N.; Zanet, P. M. J. Org. Chem. 1963, 28, 55. (e) Greene, F. D.; Savitz, M. L.; Osterholtz, F. D.; Lau, H. H.; Smith, W. N.; Zanet, P. M. J. Org. Chem. 1963, 28, 55. Also see a review: (g) Walling, C. Pure Appl. Chem. 1967, 15, 69.
36. (4) For examples of 1,5-H shift from C to O• by the photolysis of hypochlorites, see: (a) Greene, F. D.; Savitz, M. L.; Lau, H. H.; Osterholtz, F. D.; Smith, W. N. J. Am. Chem. Soc. 1961, 83, 2196. (b) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1961, 83, 2207. (c) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1961, 83, 2214. (d) Mill, J. S.; Petrov, V. Chem. Ind. 1961, 946. (e) Greene, F. D.; Savitz, M. L.; Osterholtz, F. D.; Lau, H. H.; Smith, W. N.; Zanet, P. M. J. Org. Chem. 1963, 28, 55. (f) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1963, 85, 1597. (f) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1963, 85, 1597.
37. (4) For examples of 1,5-H shift from C to O• by the photolysis of hypochlorites, see: (a) Greene, F. D.; Savitz, M. L.; Lau, H. H.; Osterholtz, F. D.; Smith, W. N. J. Am. Chem. Soc. 1961, 83, 2196. (b) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1961, 83, 2207. (c) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1961, 83, 2214. (d) Mill, J. S.; Petrov, V. Chem. Ind. 1961, 946. (e) Greene, F. D.; Savitz, M. L.; Osterholtz, F. D.; Lau, H. H.; Smith, W. N.; Zanet, P. M. J. Org. Chem. 1963, 28, 55. (f) Walling, C.; Padwa, A. J. Am. Chem. Soc. 1963, 85, 1597. Also see a review: (g) Walling, C. Pure Appl. Chem. 1967, 15, 69. Also see a review: (g) Walling, C. Pure Appl. Chem. 1967, 15, 69. (b) Smolinsky, G.; Feuer, B. I. J. Org. Chem. 1965, 30, 3216. (c) Gibson, T. W.; Erman, W. F. J. Am. Chem. Soc. 1969, 91, 4771. Also see a review: (d) Brun, P.; Waegell, B. Tetrahedron 1976, 32, 517.
38. For examples of 1,5-H shift from C to O• by the photolysis of hypobromites, see: (a) Akhtar, M.; Hunt, P.; Dewhurst, P. B. J. Am. Chem. Soc. 1965, 87, 1807. (c) Gibson, T. W.; Erman, W. F. J. Am. Chem. Soc. 1969, 91, 4771. Also see a review: (d) Brun, P.; Waegell, B. Tetrahedron 1976, 32, 517.
39. For examples of 1,5-H shift from C to O• by the photolysis of hypobromites, see: (a) Akhtar, M.; Hunt, P.; Dewhurst, P. B. J. Am. Chem. Soc. 1965, 87, 1807. (b) Smolinsky, G.; Feuer, B. I. J. Org. Chem. 1965, 30, 3216. (b) Smolinsky, G.; Feuer, B. I. J. Org. Chem. 1965, 30, 3216. Also see a review: (d) Brun, P.; Waegell, B. Tetrahedron 1976, 32, 517.
40. For examples of 1,5-H shift from C to O• by the photolysis of hypobromites, see: (a) Akhtar, M.; Hunt, P.; Dewhurst, P. B. J. Am. Chem. Soc. 1965, 87, 1807. (b) Smolinsky, G.; Feuer, B. I. J. Org. Chem. 1965, 30, 3216. (c) Gibson, T. W.; Erman, W. F. J. Am. Chem. Soc. 1969, 91, 4771. (c) Gibson, T. W.; Erman, W. F. J. Am. Chem. Soc. 1969, 91, 4771.
41. 2, see: (d) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1964, 86, 1528. In situ from alcohols and iodobenzene diacetate, see: (e) Concepción, J.-I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1984, 25, 1953. (f) Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999.
42. 2, see: (d) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1964, 86, 1528. In situ from alcohols and iodobenzene diacetate, see: (e) Concepción, J.-I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1984, 25, 1953. (f) Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999.
43. 2, see: (d) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1964, 86, 1528. In situ from alcohols and iodobenzene diacetate, see: (e) Concepción, J.-I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1984, 25, 1953. (f) Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999.
44. 2, see: (a) Meystre, C.; Heusler, K.; Kalvoda, J.; Wieland, P.; Anner, G.; Wettstein, A. Helv. Chim. Acta 1962, 45, 1317. (b) Heusler, K.; Kalvoda, J.; Meystre, C.; Anner, G.; Wettstein, A. Helv. Chim. Acta 1962, 45, 2161. Also see a review: (c) Kalvoda, J.; Heusler, K. Synthesis 1971, 501. Also see a review: (c) Kalvoda, J.; Heusler, K. Synthesis 1971, 501. In situ from alcohols and iodobenzene diacetate, see: (e) Concepción, J.-I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1984, 25, 1953. (f) Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999.
45. 2, see: (d) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1964, 86, 1528. (f) Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999.
46. 2, see: (d) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1964, 86, 1528. In situ from alcohols and iodobenzene diacetate, see: (e) Concepción, J.-I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1984, 25, 1953. In situ from alcohols and iodobenzene diacetate, see: (e) Concepción, J.-I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1984, 25, 1953.
47. 2, see: (d) Akhtar, M.; Barton, D. H. R. J. Am. Chem. Soc. 1964, 86, 1528. In situ from alcohols and iodobenzene diacetate, see: (e) Concepción, J.-I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1984, 25, 1953. (f) Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999. (f) Martín, A.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1996, 61, 3999. (b) Hernández, R.; Velázquez, S. M.; Suárez, E.; Rodríguez, M. S. J. Org. Chem. 1994, 59, 6395.
48. For examples of 1,5-H shift from C to O• by the reaction of ROH with selenium reagent, see: (a) Dorta, R. L.; Francisco, C. G.; Freire, R.; Suárez, E. Tetrahedron Lett. 1988, 29, 5429.
49. For examples of 1,5-H shift from C to O• by the reaction of ROH with selenium reagent, see: (a) Dorta, R. L.; Francisco, C. G.; Freire, R.; Suárez, E. Tetrahedron Lett. 1988, 29, 5429. (b) Hernández, R.; Velázquez, S. M.; Suárez, E.; Rodríguez, M. S. J. Org. Chem. 1994, 59, 6395. (b) Hernández, R.; Velázquez, S. M.; Suárez, E.; Rodríguez, M. S. J. Org. Chem. 1994, 59, 6395.
50. For examples of 1,5-H shift from C to O• by the homolysis of alkyl arylsulfenate, see: Pasto, D. J.; Cottard, F. Tetrahedron Lett. 1994, 35, 4303.
51. For examples of 1,5-H shift from C to O• by the reaction of ROH with Ce(IV), see: Trahanovsky, W. S.; Young, M. G.; Nave, P. M. Tetrahedron Lett. 1969, 2501.
52. For examples of 1,5-H shift from C to O• by the decomposition of peroxides, see: (a) Kochi, J. K. J. Am. Chem. Soc. 1963, 85, 1958. (c) Freerksen, R. W.; Pabst, W. E.; Raggio, M. L.; Sherman, S. A.; Wroble, R. R.; Watt, D. S. J. Am. Chem. Soc. 1977, 99, 1536. (d) Kropf, H.; von Wallis, H. Synthesis 1981, 237. (e) Čeković, Ž.; Cvetković, M. Tetrahedron Lett. 1982, 23, 3791.
53. For examples of 1,5-H shift from C to O• by the decomposition of peroxides, see: (a) Kochi, J. K. J. Am. Chem. Soc. 1963, 85, 1958. (b) Green, M. M.; Čeković, Ž. J. Am. Chem. Soc. 1974, 96, 3000. (b) Green, M. M.; Čeković, Ž. J. Am. Chem. Soc. 1974, 96, 3000. (d) Kropf, H.; von Wallis, H. Synthesis 1981, 237. (e) Čeković, Ž.; Cvetković, M. Tetrahedron Lett. 1982, 23, 3791.
54. For examples of 1,5-H shift from C to O• by the decomposition of peroxides, see: (a) Kochi, J. K. J. Am. Chem. Soc. 1963, 85, 1958. (b) Green, M. M.; Čeković, Ž. J. Am. Chem. Soc. 1974, 96, 3000. (c) Freerksen, R. W.; Pabst, W. E.; Raggio, M. L.; Sherman, S. A.; Wroble, R. R.; Watt, D. S. J. Am. Chem. Soc. 1977, 99, 1536. (c) Freerksen, R. W.; Pabst, W. E.; Raggio, M. L.; Sherman, S. A.; Wroble, R. R.; Watt, D. S. J. Am. Chem. Soc. 1977, 99, 1536. (e) Čeković, Ž.; Cvetković, M. Tetrahedron Lett. 1982, 23, 3791.
55. For examples of 1,5-H shift from C to O• by the decomposition of peroxides, see: (a) Kochi, J. K. J. Am. Chem. Soc. 1963, 85, 1958. (b) Green, M. M.; Čeković, Ž. J. Am. Chem. Soc. 1974, 96, 3000. (c) Freerksen, R. W.; Pabst, W. E.; Raggio, M. L.; Sherman, S. A.; Wroble, R. R.; Watt, D. S. J. Am. Chem. Soc. 1977, 99, 1536. (d) Kropf, H.; von Wallis, H. Synthesis 1981, 237. (d) Kropf, H.; von Wallis, H. Synthesis 1981, 237.
56. For examples of 1,5-H shift from C to O• by the decomposition of peroxides, see: (a) Kochi, J. K. J. Am. Chem. Soc. 1963, 85, 1958. (b) Green, M. M.; Čeković, Ž. J. Am. Chem. Soc. 1974, 96, 3000. (c) Freerksen, R. W.; Pabst, W. E.; Raggio, M. L.; Sherman, S. A.; Wroble, R. R.; Watt, D. S. J. Am. Chem. Soc. 1977, 99, 1536. (d) Kropf, H.; von Wallis, H. Synthesis 1981, 237. (e) Čeković, Ž.; Cvetković, M. Tetrahedron Lett. 1982, 23, 3791. (e) Čeković, Ž.; Cvetković, M. Tetrahedron Lett. 1982, 23, 3791. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
57. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
58. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
59. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
60. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
61. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
62. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
63. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
64. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
65. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
66. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
67. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
68. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
69. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
70. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461.
71. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407.
72. For examples of 1,5-H shift from C to O• via a ring opening of α-oxiranylcarbinyl radicals and the subsequent 5-exo cyclization, see: (a) Rawal, V. H.; Newton, R. C.; Krishnamurthy, V. J. Org. Chem. 1990, 55, 5181. (b) Kim, S.; Lee, S.; Koh, J. S. J. Am. Chem. Soc. 1991, 113, 5106. (c) Begley, M. J.; Housden, N.; Johns, A.; Murphy, J. A. Tetrahedron 1991, 47, 8417. (d) Rawal, V. H.; Krishnamurthy, V. Tetrahedron Lett. 1992, 33, 3439. (e) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687. (f) Kim, S.; Koh, J. S. J. Chem. Soc., Chem. Commun. 1992, 1377. (g) Kim, S.; Koh, J. S. Tetrahedron Lett. 1992, 33, 7391. (h) Breen, A. P.; Murphy, J. A. J. Chem. Soc., Chem. Commun. 1993, 191. (i) Galatsis, P.; Millan, S. D.; Faber, T. J. Org. Chem. 1993, 55, 1215. (j) Rawal, V. H.; Krishnamurthy, V.; Fabre, A. Tetrahedron Lett. 1993, 34, 2899. (k) Kim, S.; Do, J. Y.; Lim, K. M. Chem. Lett. 1996, 669. Also see: (l) Čeković, Ž.; Ilijev, D. Tetrahedron Lett. 1988, 29, 1441. For examples of 1,5-H shift of the α-cyanoalkoxyl radical and the subsequent CN migration to form δ-cyano ketone, see: (m) Kalvoda, J.; Botta, L. Helv. Chim. Acta 1972, 55, 356. Also see refs 10c and 13h. For reviews of γ-hydrogen abstraction (1,5-H shift from C to O•) by the photolysis of aromatic ketones and the subsequent radical-radical coupling to form cyclobutanols (Norrish type-II reaction), see: (n) Wagner, P. J. Acc. Chem. Res. 1971, 4, 168. (o) Kanaoka, Y. Acc. Chem. Res. 1978, 11, 407. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461. (p) Wagner, P. J. Acc. Chem. Res. 1983, 16, 461. (b) Petrović, G.; Čeković, Ž. Tetrahedron Lett. 1997, 38, 627. (c) Petrović, G. Saičić, R. N.; Čeković, Ž. Tetrahedron Lett. 1997, 38, 7107.
73. For intermolecular exceptions, see: (a) Lopez, J. C.; Alonso, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 6471. (c) Petrović, G. Saičić, R. N.; Čeković, Ž. Tetrahedron Lett. 1997, 38, 7107.
74. For intermolecular exceptions, see: (a) Lopez, J. C.; Alonso, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 6471. (b) Petrović, G.; Čeković, Ž. Tetrahedron Lett. 1997, 38, 627. (b) Petrović, G.; Čeković, Ž. Tetrahedron Lett. 1997, 38, 627.
75. For intermolecular exceptions, see: (a) Lopez, J. C.; Alonso, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 6471. (b) Petrović, G.; Čeković, Ž. Tetrahedron Lett. 1997, 38, 627. (c) Petrović, G. Saičić, R. N.; Čeković, Ž. Tetrahedron Lett. 1997, 38, 7107. (c) Petrović, G. Saičić, R. N.; Čeković, Ž. Tetrahedron Lett. 1997, 38, 7107. (b) Mićović, V. M.; Mamuzić, R. I.; Jeremić, D.; Mihailović, M. L. Tetrahedron 1964, 20, 2279. (c) Mihailović, M. L.; Čeković, Ž.; Maksimović, Z.; Jeremić, D.; Lorenc, L.; Mamuzić, R. I. Tetrahedron 1965, 21, 2799. For leading reviews, see: (d) Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525. (e) Mihailović, M. L.; Čeković, Ž. Synthesis 1970, 209. (f) Rotermund, G. W. In Methoden der Organischen Chemie (Houben-Weyl); Müller, E., Ed.; Georg Thieme: Stuttgart, 1975, Band 4, Teil 1b, Oxidation II, p 204. (g) Rubottom, G. M. In Oxidation in Organic Chemistry; Academic Press: New York, 1982; part D, Chapter I. (h) Mihailović, M. L.; Čeković, Ž.; Lorenc, L. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York 1986; Chapter 14.
76. For pioneering work on THF-formation by oxidative cyclization of alcohols with LTA, see: (a) Cainelli, G.; Mihaitović, M. L.; Arigoni, D.; Jeger, O. Helv. Chim. Acta 1959, 42, 1124. (c) Mihailović, M. L.; Čeković, Ž.; Maksimović, Z.; Jeremić, D.; Lorenc, L.; Mamuzić, R. I. Tetrahedron 1965, 21, 2799. For leading reviews, see: (d) Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525. (e) Mihailović, M. L.; Čeković, Ž. Synthesis 1970, 209. (f) Rotermund, G. W. In Methoden der Organischen Chemie (Houben-Weyl); Müller, E., Ed.; Georg Thieme: Stuttgart, 1975, Band 4, Teil 1b, Oxidation II, p 204. (g) Rubottom, G. M. In Oxidation in Organic Chemistry; Academic Press: New York, 1982; part D, Chapter I. (h) Mihailović, M. L.; Čeković, Ž.; Lorenc, L. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York 1986; Chapter 14.
77. (13) For pioneering work on THF-formation by oxidative cyclization of alcohols with LTA, see: (a) Cainelli, G.; Mihaitović, M. L.; Arigoni, D.; Jeger, O. Helv. Chim. Acta 1959, 42, 1124. (b) Mićović, V. M.; Mamuzić, R. I.; Jeremić, D.; Mihailović, M. L. Tetrahedron 1964, 20, 2279. (b) Mićović, V. M.; Mamuzić, R. I.; Jeremić, D.; Mihailović, M. L. Tetrahedron 1964, 20, 2279. For leading reviews, see: (d) Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525. (e) Mihailović, M. L.; Čeković, Ž. Synthesis 1970, 209. (f) Rotermund, G. W. In Methoden der Organischen Chemie (Houben-Weyl); Müller, E., Ed.; Georg Thieme: Stuttgart, 1975, Band 4, Teil 1b, Oxidation II, p 204. (g) Rubottom, G. M. In Oxidation in Organic Chemistry; Academic Press: New York, 1982; part D, Chapter I. (h) Mihailović, M. L.; Čeković, Ž.; Lorenc, L. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York 1986; Chapter 14.
78. (13) For pioneering work on THF-formation by oxidative cyclization of alcohols with LTA, see: (a) Cainelli, G.; Mihaitović, M. L.; Arigoni, D.; Jeger, O. Helv. Chim. Acta 1959, 42, 1124. (b) Mićović, V. M.; Mamuzić, R. I.; Jeremić, D.; Mihailović, M. L. Tetrahedron 1964, 20, 2279. (c) Mihailović, M. L.; Čeković, Ž.; Maksimović, Z.; Jeremić, D.; Lorenc, L.; Mamuzić, R. I. Tetrahedron 1965, 21, 2799. (c) Mihailović, M. L.; Čeković, Ž.; Maksimović, Z.; Jeremić, D.; Lorenc, L.; Mamuzić, R. I. Tetrahedron 1965, 21, 2799. (e) Mihailović, M. L.; Čeković, Ž. Synthesis 1970, 209. (f) Rotermund, G. W. In Methoden der Organischen Chemie (Houben-Weyl); Müller, E., Ed.; Georg Thieme: Stuttgart, 1975, Band 4, Teil 1b, Oxidation II, p 204. (g) Rubottom, G. M. In Oxidation in Organic Chemistry; Academic Press: New York, 1982; part D, Chapter I. (h) Mihailović, M. L.; Čeković, Ž.; Lorenc, L. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York 1986; Chapter 14.
79. (13) For pioneering work on THF-formation by oxidative cyclization of alcohols with LTA, see: (a) Cainelli, G.; Mihaitović, M. L.; Arigoni, D.; Jeger, O. Helv. Chim. Acta 1959, 42, 1124. (b) Mićović, V. M.; Mamuzić, R. I.; Jeremić, D.; Mihailović, M. L. Tetrahedron 1964, 20, 2279. (c) Mihailović, M. L.; Čeković, Ž.; Maksimović, Z.; Jeremić, D.; Lorenc, L.; Mamuzić, R. I. Tetrahedron 1965, 21, 2799. For leading reviews, see: (d) Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525. For leading reviews, see: (d) Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525. (f) Rotermund, G. W. In Methoden der Organischen Chemie (Houben-Weyl); Müller, E., Ed.; Georg Thieme: Stuttgart, 1975, Band 4, Teil 1b, Oxidation II, p 204. (g) Rubottom, G. M. In Oxidation in Organic Chemistry; Academic Press: New York, 1982; part D, Chapter I. (h) Mihailović, M. L.; Čeković, Ž.; Lorenc, L. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York 1986; Chapter 14.
80. (13) For pioneering work on THF-formation by oxidative cyclization of alcohols with LTA, see: (a) Cainelli, G.; Mihaitović, M. L.; Arigoni, D.; Jeger, O. Helv. Chim. Acta 1959, 42, 1124. (b) Mićović, V. M.; Mamuzić, R. I.; Jeremić, D.; Mihailović, M. L. Tetrahedron 1964, 20, 2279. (c) Mihailović, M. L.; Čeković, Ž.; Maksimović, Z.; Jeremić, D.; Lorenc, L.; Mamuzić, R. I. Tetrahedron 1965, 21, 2799. For leading reviews, see: (d) Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525. (e) Mihailović, M. L.; Čeković, Ž. Synthesis 1970, 209. (e) Mihailović, M. L.; Čeković, Ž. Synthesis 1970, 209. (g) Rubottom, G. M. In Oxidation in Organic Chemistry; Academic Press: New York, 1982; part D, Chapter I. (h) Mihailović, M. L.; Čeković, Ž.; Lorenc, L. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York 1986; Chapter 14.
81. (13) For pioneering work on THF-formation by oxidative cyclization of alcohols with LTA, see: (a) Cainelli, G.; Mihaitović, M. L.; Arigoni, D.; Jeger, O. Helv. Chim. Acta 1959, 42, 1124. (b) Mićović, V. M.; Mamuzić, R. I.; Jeremić, D.; Mihailović, M. L. Tetrahedron 1964, 20, 2279. (c) Mihailović, M. L.; Čeković, Ž.; Maksimović, Z.; Jeremić, D.; Lorenc, L.; Mamuzić, R. I. Tetrahedron 1965, 21, 2799. For leading reviews, see: (d) Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525. (e) Mihailović, M. L.; Čeković, Ž. Synthesis 1970, 209. (f) Rotermund, G. W. In Methoden der Organischen Chemie (Houben-Weyl); Müller, E., Ed.; Georg Thieme: Stuttgart, 1975, Band 4, Teil 1b, Oxidation II, p 204. (f) Rotermund, G. W. In Methoden der Organischen Chemie (Houben-Weyl); Müller, E., Ed.; Georg Thieme: Stuttgart, 1975, Band 4, Teil 1b, Oxidation II, p 204. (h) Mihailović, M. L.; Čeković, Ž.; Lorenc, L. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York 1986; Chapter 14.
82. (13) For pioneering work on THF-formation by oxidative cyclization of alcohols with LTA, see: (a) Cainelli, G.; Mihaitović, M. L.; Arigoni, D.; Jeger, O. Helv. Chim. Acta 1959, 42, 1124. (b) Mićović, V. M.; Mamuzić, R. I.; Jeremić, D.; Mihailović, M. L. Tetrahedron 1964, 20, 2279. (c) Mihailović, M. L.; Čeković, Ž.; Maksimović, Z.; Jeremić, D.; Lorenc, L.; Mamuzić, R. I. Tetrahedron 1965, 21, 2799. For leading reviews, see: (d) Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525. (e) Mihailović, M. L.; Čeković, Ž. Synthesis 1970, 209. (f) Rotermund, G. W. In Methoden der Organischen Chemie (Houben-Weyl); Müller, E., Ed.; Georg Thieme: Stuttgart, 1975, Band 4, Teil 1b, Oxidation II, p 204. (g) Rubottom, G. M. In Oxidation in Organic Chemistry; Academic Press: New York, 1982; part D, Chapter I. (g) Rubottom, G. M. In Oxidation in Organic Chemistry; Academic Press: New York, 1982; part D, Chapter I.
83. (13) For pioneering work on THF-formation by oxidative cyclization of alcohols with LTA, see: (a) Cainelli, G.; Mihaitović, M. L.; Arigoni, D.; Jeger, O. Helv. Chim. Acta 1959, 42, 1124. (b) Mićović, V. M.; Mamuzić, R. I.; Jeremić, D.; Mihailović, M. L. Tetrahedron 1964, 20, 2279. (c) Mihailović, M. L.; Čeković, Ž.; Maksimović, Z.; Jeremić, D.; Lorenc, L.; Mamuzić, R. I. Tetrahedron 1965, 21, 2799. For leading reviews, see: (d) Heusler, K.; Kalvoda, J. Angew. Chem., Int. Ed. Engl. 1964, 3, 525. (e) Mihailović, M. L.; Čeković, Ž. Synthesis 1970, 209. (f) Rotermund, G. W. In Methoden der Organischen Chemie (Houben-Weyl); Müller, E., Ed.; Georg Thieme: Stuttgart, 1975, Band 4, Teil 1b, Oxidation II, p 204. (g) Rubottom, G. M. In Oxidation in Organic Chemistry; Academic Press: New York, 1982; part D, Chapter I. (h) Mihailović, M. L.; Čeković, Ž.; Lorenc, L. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York 1986; Chapter 14. (h) Mihailović, M. L.; Čeković, Ž.; Lorenc, L. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York 1986; Chapter 14.
84. Ryu, I.; Alper, H. J. Am. Chem. Soc. 1993, 115, 7543. Also see ref 15e.
85. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
86. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
87. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
88. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
89. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
90. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
91. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
92. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
93. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
94. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
95. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
96. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
97. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
98. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
99. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
100. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
101. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi,
102. For recent reports on free-radical carbonylation, see: (a) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Fukushima, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1996, 118, 10670. (b) Ryu, I.; Muraoka, H.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1996, 61, 6396. (c) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett. 1996, 37, 6729. (d) Brinza, I. M.; Fallis, A. G. J. Org. Chem. 1996, 67, 3580. (e) Okuro, K.; Alper, H. J. Org. Chem. 1996, 61, 5312. (f) Chatgilialoglu, C.; Ferreri, C.; Sommazzi, A. J. Am. Chem. Soc. 1996, 118, 7223. (g) Ryu, I.; Nagahara, K.; Kurihara, A.; Komatsu, M.; Sonoda, N. J. Organomet. Chem. 1997, 548, 105. (h) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465. (i) Tsunoi, S.; Ryu, I.; Yamasaki, S.; Tanaka, M.; Sonoda, N.; Komatsu, M. Chem. Commun. 1997, 1889. (j) Ryu, I.; Okuda, T.; Nagahara, K.; Kambe, N.; Komatsu, M.; Sonoda, N. J. Org. Chem. 1997, 62, 7550. (k) Nagahara, K.; Ryu, I.; Yamazaki, H.; Kambe, N.; Komatsu, M.; Sonoda, N.; Baba, A. Tetrahedron 1997, 53, 14615. (l) Ryu, I.; Fukushima, H.; Okuda, T.; Matsu, K.; Kambe, N.; Sonoda, N.; Komatsu, M. Synlett 1997, 1265. (m) Ryu, I.; Niguma, T.; Minakata, S.; Komatsu, M.; Hadida, S.; Curran, D. P. Tetrahedron Lett. 1997, 38, 7883. (n) Kato, S.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 1998, 63, 222. (o) Curran, D. P.; Sisko, J.; Balog, A.; Sonoda, N.; Nagahara, K.; Ryu, I. J. Chem. Soc., Perkin Trans. 1 1998, 1591. (p) Ryu, I.; Matsu, K.; Minakata, S.; Komatsu, M. J. Am. Chem. Soc. 1998, 120, 5838. Also see reviews: (q) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050. (r) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
103. A part of this work has appeared in preliminary form, see: Tsunoi, S.; Ryu, I.; Sonoda, N. J. Am. Chem. Soc. 1994, 116, 5473.
104. For examples of 1,6-H shift, see: (a) Kay, I. T.; Williams, E. G. Tetrahedron Lett. 1983, 24, 5915. Also see a review: (c) Wagner, P. J. Acc. Chem. Res. 1989, 22, 83.
105. (17) For examples of 1,6-H shift, see: (a) Kay, I. T.; Williams, E. G. Tetrahedron Lett. 1983, 24, 5915. (b) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G. Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117. (b) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G. Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117.
106. (17) For examples of 1,6-H shift, see: (a) Kay, I. T.; Williams, E. G. Tetrahedron Lett. 1983, 24, 5915. (b) Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G. Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117. Also see a review: (c) Wagner, P. J. Acc. Chem. Res. 1989, 22, 83. Also see a review: (c) Wagner, P. J. Acc. Chem. Res. 1989, 22, 83. (b) Brunton, G.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 6803. (c) Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085. (d) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893.
107. A product formed via 1,4-hydrogen transfer was not detected with 3-pentanol and 2,4-dimethyl-3-pentanol. For examples of 1,4-hydrogen-transfer reactions, see: (a) Wallace, T. J.; Gritter, R. J. J. Org. Chem. 1961, 26, 5256. (c) Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085. (d) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893.
108. (18) A product formed via 1,4-hydrogen transfer was not detected with 3-pentanol and 2,4-dimethyl-3-pentanol. For examples of 1,4-hydrogen-transfer reactions, see: (a) Wallace, T. J.; Gritter, R. J. J. Org. Chem. 1961, 26, 5256. (b) Brunton, G.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 6803. (b) Brunton, G.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 6803. (d) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893.
109. (18) A product formed via 1,4-hydrogen transfer was not detected with 3-pentanol and 2,4-dimethyl-3-pentanol. For examples of 1,4-hydrogen-transfer reactions, see: (a) Wallace, T. J.; Gritter, R. J. J. Org. Chem. 1961, 26, 5256. (b) Brunton, G.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 6803. (c) Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085. (c) Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085.
110. (18) A product formed via 1,4-hydrogen transfer was not detected with 3-pentanol and 2,4-dimethyl-3-pentanol. For examples of 1,4-hydrogen-transfer reactions, see: (a) Wallace, T. J.; Gritter, R. J. J. Org. Chem. 1961, 26, 5256. (b) Brunton, G.; Griller, D.; Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1976, 98, 6803. (c) Journet, M.; Malacria, M. J. Org. Chem. 1992, 57, 3085. (d) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893. (d) Journet, M.; Malacria, M. Tetrahedron Lett. 1992, 33, 1893.
111. For example, with Im, ε-lactone was not detected. We speculate that, in this case, 1,6-H transfer yields a tertiary radical, which would easily undergo the subsequent oxidation to give the carbocation rather than CO trapping (Table 3, run 3).
112. Wheeler, J. W.; Evans, S. L.; Blum, M. S.; Velthius, H. H. V.; de Camargo, J. M. F. Tetrahedron Lett. 1976, 4029.
113. (a) Pirkle, W. H.; Adams, P. E. J. Org. Chem. 1978, 43, 378.
114. (b) Bacardit, R.; Moreno-Mañas, M. J. Chem. Ecol. 1983, 9, 703.
115. (c) Mori, K.; Senda, S. Tetrahedron 1985, 41, 541.
116. (d) Bäckvall, J.-E.; Byström, S. E.; Nyström, J. E. Tetrahedron 1985, 41, 5761.
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126. (n) Jacobs, H. K.; Mueller, B. H.; Gopalan, A. S. Tetrahedron 1992, 48, 8891.
127. For LTA-induced carbonylation via β scission of cyclic alkoxyl radicals, see: Tsunoi, S.; Ryu, I.; Tamura, Y.; Yamasaki, S.; Sonoda, N. Synlett 1994, 1009.
128. Heusler, K.; Kalvoda, J.; Anner, G.; Wettstein, A. Helv. Chim. Acta 1963, 46, 352.
129. (a) Beckwith, A. L. J.: Hay, B. P. J. Am. Chem. Soc. 1989, 111, 2674.
130. -1 (for n-hexyloxy radical), see: (b) Gilbert, B. C.; Holmes, R. G. G.; Laue, H. A. H.; Norman, R. O. C. J. Chem. Soc., Perkin Trans. 2 1976, 1047.
131. The reason for the observed low conversion under low CO pressure conditions remains uncertain.
132. Wayner, D. D. M.; Griller, D. In Advances Free Radical Chemistry; Tanner, D. D., Ed.; JAI Press: Greenwich, 1990; Vol. 1, p 159. The preference of methylene over methyl in the competitive 1,5-H abstraction of alkoxyl radical has been documented. See refs 4e-g.
133. The material balance is fairly poor (70-80%), which may be attributed in part to the formation of fragmentation products.
134. 3 in the ring opening of bicyclic siloxycyclopropanes with LTA, see: Rubottom, R. G.; Beedle, E. C.; Kim, C.-W.; Mott, R. C. J. Am. Chem. Soc. 1985, 107, 4230.
135. Čeković and co-workers proposed that in the case of the LTA-oxidation system, the δ-hydroxyalkyl radical is in a tight radical pair with Pb(III) since the major product from 8-nonen-1-ol was the THF derivative formed via oxidative cyclization rather than the cyclopentane derivative formed via 5-exo cyclization. See ref 111. Also see: Mihailović, M. L.; Konstantinović, S.; Vukićević, R. J. Serb. Chem. Soc. 1987, 52, 175.
136. Hauser, D.; Schaffner, K.; Jeger, O. Helv. Chim. Acta 1964, 47, 1883.
137. For the decarbonylation order of the acyl radical being tertiary > secondary > primary acyl radical, see: (a) Chatgilialoglu, C.; Lucarini, M. Tetrahedron Lett. 1995, 36, 1299.
138. For the decarbonylation order of the acyl radical being tertiary > secondary > primary acyl radical, see: (a) Chatgilialoglu, C.; Lucarini, M. Tetrahedron Lett. 1995, 36, 1299. (b) Chatgilialoglu, C.; Ferreri, C.; Lucarini, M.; Pedrielli, P.; Pedulli, G. F. Organometallics 1995, 14, 2672. (b) Chatgilialoglu, C.; Ferreri, C.; Lucarini, M.; Pedrielli, P.; Pedulli, G. F. Organometallics 1995, 14, 2672.
139. (a) Mihailović, M. L.; Čeković, Ž.; Stanković, J.; Pavlović, N.; Konstantinović, S.; Dokić-Mazinjanin, S. Helv. Chim. Acta 1973, 56, 3056.
140. (b) Bortrand, M. P.; Surzur, J. M.; Boyer, M.; Mihailović, M. L. Tetrahedron 1979, 35, 1365.
141. The formation of 3z may be accounted for by the cyclization of the alkoxyl radical onto internal C==C and the subsequent oxidation of the cyclized primary radical. The carbonylation of the primary radical does not appear to compete well with the oxidation to yield the acetoxylated product. It seems probable that stabilization of the three-membered oxonium cation contributes to this facile oxidation of the primary radical β to oxygen. For an alternative pathway involving coordination of C==C to Pb, see: (a) Moriarty, R. M.; Kapadia, K. Tetrahedron Lett. 1964, 1165.
142. The formation of 3z may be accounted for by the cyclization of the alkoxyl radical onto internal C==C and the subsequent oxidation of the cyclized primary radical. The carbonylation of the primary radical does not appear to compete well with the oxidation to yield the acetoxylated product. It seems probable that stabilization of the three-membered oxonium cation contributes to this facile oxidation of the primary radical β to oxygen. For an alternative pathway involving coordination of C==C to Pb, see: (a) Moriarty, R. M.; Kapadia, K. Tetrahedron Lett. 1964, 1165. (b) Moon, S.; Lodge, J. M. J. Org. Chem. 1964, 29, 3453. (b) Moon, S.; Lodge, J. M. J. Org. Chem. 1964, 29, 3453. (b) Fraser-Reid, B.; Vite, G. D.; Yeung, B. A.; Tsang, R. Tetrahedron Lett. 1988, 29, 1645. Also see ref 12a.
143. For examples of the generation of alkoxyl radicals from nitrate esters, see: (a) Vite, G, D.; Fraser-Reid, B. Synth. Commun. 1988, 18, 1339.
144. (34) For examples of the generation of alkoxyl radicals from nitrate esters, see: (a) Vite, G, D.; Fraser-Reid, B. Synth. Commun. 1988, 18, 1339. (b) Fraser-Reid, B.; Vite, G. D.; Yeung, B. A.; Tsang, R. Tetrahedron Lett. 1988, 29, 1645. Also see ref 12a. (b) Fraser-Reid, B.; Vite, G. D.; Yeung, B. A.; Tsang, R. Tetrahedron Lett. 1988, 29, 1645. Also see ref 12a. (b) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (c) Hartung, J.; Hiller, M.; Schmidt, P. Chem. Eur. J. 1996, 2, 1014. (d) Hartung, J.; Hiller, M.; Schmidt, P. Liebigs Ann. 1996, 1425. (e) Hartung, J.; Schwarz, M. Synlett 1997, 848.
145. For examples of the generation of alkoxyl radicals from N-alkoxypyridinethiones and their derivatives, see: (a) Beckwith, A. L. J.: Hay, B. P. J. Am. Chem. Soc. 1988, 110, 4415. (c) Hartung, J.; Hiller, M.; Schmidt, P. Chem. Eur. J. 1996, 2, 1014. (d) Hartung, J.; Hiller, M.; Schmidt, P. Liebigs Ann. 1996, 1425. (e) Hartung, J.; Schwarz, M. Synlett 1997, 848.
146. For examples of the generation of alkoxyl radicals from N-alkoxypyridinethiones and their derivatives, see: (a) Beckwith, A. L. J.: Hay, B. P. J. Am. Chem. Soc. 1988, 110, 4415. (b) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (b) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (d) Hartung, J.; Hiller, M.; Schmidt, P. Liebigs Ann. 1996, 1425. (e) Hartung, J.; Schwarz, M. Synlett 1997, 848.
147. For examples of the generation of alkoxyl radicals from N-alkoxypyridinethiones and their derivatives, see: (a) Beckwith, A. L. J.: Hay, B. P. J. Am. Chem. Soc. 1988, 110, 4415. (b) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (c) Hartung, J.; Hiller, M.; Schmidt, P. Chem. Eur. J. 1996, 2, 1014. (c) Hartung, J.; Hiller, M.; Schmidt, P. Chem. Eur. J. 1996, 2, 1014. (e) Hartung, J.; Schwarz, M. Synlett 1997, 848.
148. For examples of the generation of alkoxyl radicals from N-alkoxypyridinethiones and their derivatives, see: (a) Beckwith, A. L. J.: Hay, B. P. J. Am. Chem. Soc. 1988, 110, 4415. (b) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (c) Hartung, J.; Hiller, M.; Schmidt, P. Chem. Eur. J. 1996, 2, 1014. (d) Hartung, J.; Hiller, M.; Schmidt, P. Liebigs Ann. 1996, 1425. (d) Hartung, J.; Hiller, M.; Schmidt, P. Liebigs Ann. 1996, 1425.
149. For examples of the generation of alkoxyl radicals from N-alkoxypyridinethiones and their derivatives, see: (a) Beckwith, A. L. J.: Hay, B. P. J. Am. Chem. Soc. 1988, 110, 4415. (b) Hartung, J.; Gallou, F. J. Org. Chem. 1995, 60, 6706. (c) Hartung, J.; Hiller, M.; Schmidt, P. Chem. Eur. J. 1996, 2, 1014. (d) Hartung, J.; Hiller, M.; Schmidt, P. Liebigs Ann. 1996, 1425. (e) Hartung, J.; Schwarz, M. Synlett 1997, 848. (e) Hartung, J.; Schwarz, M. Synlett 1997, 848.
150. (a) Beckwith, A. L. J.; Hay, B. P.; Wolliams, G. M. J. Chem. Soc., Chem. Commun. 1989, 1202.
151. (b) Pasto, D. J.; L'Hermine, G. J. Org. Chem. 1990, 55, 5815.
152. (c) Pasto, D. J.; L'Hermine, G. Tetrahedron 1993, 49, 3259. Also see refs 8 and 12c.
153. Photolysis was carried out using a stainless autoclave with quartz glass. Schematic photoirradiation apparatus is given in the Supporting Information in ref 15b.
154. For atom and group transfer reactions to acyl radicals, see: (a) Walling, C.; Basedow, O. H.; Savas, E. S. J. Am. Chem. Soc. 1960, 82, 2181. (c) Crich, D.; Chen, C.; Hwang, J.-T.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937. Also see refs 15a, b, h, and j.
155. For atom and group transfer reactions to acyl radicals, see: (a) Walling, C.; Basedow, O. H.; Savas, E. S. J. Am. Chem. Soc. 1960, 82, 2181. (b) Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc., Perkin Trans. 1 1990, 2721. (b) Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc., Perkin Trans. 1 1990, 2721.
156. For atom and group transfer reactions to acyl radicals, see: (a) Walling, C.; Basedow, O. H.; Savas, E. S. J. Am. Chem. Soc. 1960, 82, 2181. (b) Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc., Perkin Trans. 1 1990, 2721. (c) Crich, D.; Chen, C.; Hwang, J.-T.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937. Also see refs 15a, b, h, and j. (c) Crich, D.; Chen, C.; Hwang, J.-T.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937. Also see refs 15a, b, h, and j.
157. The detailed results of δ-carbonylation using photolysis of alkyl benzenesulfenates will be reported in a separate paper.
158. For leading references, see: (a) Endo, A.; Kurodo, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. (c) Wovkulich, P. M.; Tang, P. C.; Chadha, N. K.; Batcho, A. D.; Barrish, J. C.; Uskokovic, M. R. J. Am. Chem. Soc. 1989, 111, 2596. (d) Danishefsky, S. J.; Simoneau, B. J. Am. Chem. Soc. 1989, 111, 2599. (e) Liu, Z.-Y.; He, L.; Zheng, H. Synlett 1993, 191. (f) Shin, I.; Zhou, H.-Q.; Que, N. L. S.; Liu, H.-W.; Swedenborg, P. D.; Jones, R. L. J. Org. Chem. 1993, 58, 2923. Also see a review: (g) Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron 1997, 53, 14507.
159. (40) For leading references, see: (a) Endo, A.; Kurodo, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. (b) Ranieri, R. L.; Calton, G. J. Tetrahedron Lett. 1978, 499. (b) Ranieri, R. L.; Calton, G. J. Tetrahedron Lett. 1978, 499. (d) Danishefsky, S. J.; Simoneau, B. J. Am. Chem. Soc. 1989, 111, 2599. (e) Liu, Z.-Y.; He, L.; Zheng, H. Synlett 1993, 191. (f) Shin, I.; Zhou, H.-Q.; Que, N. L. S.; Liu, H.-W.; Swedenborg, P. D.; Jones, R. L. J. Org. Chem. 1993, 58, 2923. Also see a review: (g) Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron 1997, 53, 14507.
160. (40) For leading references, see: (a) Endo, A.; Kurodo, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. (b) Ranieri, R. L.; Calton, G. J. Tetrahedron Lett. 1978, 499. (c) Wovkulich, P. M.; Tang, P. C.; Chadha, N. K.; Batcho, A. D.; Barrish, J. C.; Uskokovic, M. R. J. Am. Chem. Soc. 1989, 111, 2596. (c) Wovkulich, P. M.; Tang, P. C.; Chadha, N. K.; Batcho, A. D.; Barrish, J. C.; Uskokovic, M. R. J. Am. Chem. Soc. 1989, 111, 2596. (e) Liu, Z.-Y.; He, L.; Zheng, H. Synlett 1993, 191. (f) Shin, I.; Zhou, H.-Q.; Que, N. L. S.; Liu, H.-W.; Swedenborg, P. D.; Jones, R. L. J. Org. Chem. 1993, 58, 2923. Also see a review: (g) Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron 1997, 53, 14507.
161. (40) For leading references, see: (a) Endo, A.; Kurodo, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. (b) Ranieri, R. L.; Calton, G. J. Tetrahedron Lett. 1978, 499. (c) Wovkulich, P. M.; Tang, P. C.; Chadha, N. K.; Batcho, A. D.; Barrish, J. C.; Uskokovic, M. R. J. Am. Chem. Soc. 1989, 111, 2596. (d) Danishefsky, S. J.; Simoneau, B. J. Am. Chem. Soc. 1989, 111, 2599. (d) Danishefsky, S. J.; Simoneau, B. J. Am. Chem. Soc. 1989, 111, 2599. (f) Shin, I.; Zhou, H.-Q.; Que, N. L. S.; Liu, H.-W.; Swedenborg, P. D.; Jones, R. L. J. Org. Chem. 1993, 58, 2923. Also see a review: (g) Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron 1997, 53, 14507.
162. (40) For leading references, see: (a) Endo, A.; Kurodo, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. (b) Ranieri, R. L.; Calton, G. J. Tetrahedron Lett. 1978, 499. (c) Wovkulich, P. M.; Tang, P. C.; Chadha, N. K.; Batcho, A. D.; Barrish, J. C.; Uskokovic, M. R. J. Am. Chem. Soc. 1989, 111, 2596. (d) Danishefsky, S. J.; Simoneau, B. J. Am. Chem. Soc. 1989, 111, 2599. (e) Liu, Z.-Y.; He, L.; Zheng, H. Synlett 1993, 191. (e) Liu, Z.-Y.; He, L.; Zheng, H. Synlett 1993, 191. Also see a review: (g) Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron 1997, 53, 14507.
163. (40) For leading references, see: (a) Endo, A.; Kurodo, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. (b) Ranieri, R. L.; Calton, G. J. Tetrahedron Lett. 1978, 499. (c) Wovkulich, P. M.; Tang, P. C.; Chadha, N. K.; Batcho, A. D.; Barrish, J. C.; Uskokovic, M. R. J. Am. Chem. Soc. 1989, 111, 2596. (d) Danishefsky, S. J.; Simoneau, B. J. Am. Chem. Soc. 1989, 111, 2599. (e) Liu, Z.-Y.; He, L.; Zheng, H. Synlett 1993, 191. (f) Shin, I.; Zhou, H.-Q.; Que, N. L. S.; Liu, H.-W.; Swedenborg, P. D.; Jones, R. L. J. Org. Chem. 1993, 58, 2923. (f) Shin, I.; Zhou, H.-Q.; Que, N. L. S.; Liu, H.-W.; Swedenborg, P. D.; Jones, R. L. J. Org. Chem. 1993, 58, 2923.
164. (40) For leading references, see: (a) Endo, A.; Kurodo, M.; Tsujita, Y. J. Antibiot. 1976, 29, 1346. (b) Ranieri, R. L.; Calton, G. J. Tetrahedron Lett. 1978, 499. (c) Wovkulich, P. M.; Tang, P. C.; Chadha, N. K.; Batcho, A. D.; Barrish, J. C.; Uskokovic, M. R. J. Am. Chem. Soc. 1989, 111, 2596. (d) Danishefsky, S. J.; Simoneau, B. J. Am. Chem. Soc. 1989, 111, 2599. (e) Liu, Z.-Y.; He, L.; Zheng, H. Synlett 1993, 191. (f) Shin, I.; Zhou, H.-Q.; Que, N. L. S.; Liu, H.-W.; Swedenborg, P. D.; Jones, R. L. J. Org. Chem. 1993, 58, 2923. Also see a review: (g) Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron 1997, 53, 14507. Also see a review: (g) Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron 1997, 53, 14507. (b) Alper, H.; Leonard, D. J. Chem. Soc., Chem. Commun. 1985, 511. (c) Chenal, T.; Naigre, R.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1993, 747. (d) Naigre, R.; Chenal, T.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Organomet. Chem. 1994, 480, 91. (e) Chow, Y. L.; Huang, Y.-J.; Dragojlovic, V. Can. J. Chem. 1995, 73, 740.
165. For selected examples of metal-mediated carbonylation of unsaturated alcohols to lead to δ-lactones, see: (a) Murray, T. F.; Varma, V.; Norton, J. R. J. Org. Chem. 1978, 43, 353. (c) Chenal, T.; Naigre, R.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1993, 747. (d) Naigre, R.; Chenal, T.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Organomet. Chem. 1994, 480, 91. (e) Chow, Y. L.; Huang, Y.-J.; Dragojlovic, V. Can. J. Chem. 1995, 73, 740.
166. For selected examples of metal-mediated carbonylation of unsaturated alcohols to lead to δ-lactones, see: (a) Murray, T. F.; Varma, V.; Norton, J. R. J. Org. Chem. 1978, 43, 353. (b) Alper, H.; Leonard, D. J. Chem. Soc., Chem. Commun. 1985, 511. (b) Alper, H.; Leonard, D. J. Chem. Soc., Chem. Commun. 1985, 511. (d) Naigre, R.; Chenal, T.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Organomet. Chem. 1994, 480, 91. (e) Chow, Y. L.; Huang, Y.-J.; Dragojlovic, V. Can. J. Chem. 1995, 73, 740.
167. For selected examples of metal-mediated carbonylation of unsaturated alcohols to lead to δ-lactones, see: (a) Murray, T. F.; Varma, V.; Norton, J. R. J. Org. Chem. 1978, 43, 353. (b) Alper, H.; Leonard, D. J. Chem. Soc., Chem. Commun. 1985, 511. (c) Chenal, T.; Naigre, R.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1993, 747. (c) Chenal, T.; Naigre, R.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1993, 747. (e) Chow, Y. L.; Huang, Y.-J.; Dragojlovic, V. Can. J. Chem. 1995, 73, 740.
168. For selected examples of metal-mediated carbonylation of unsaturated alcohols to lead to δ-lactones, see: (a) Murray, T. F.; Varma, V.; Norton, J. R. J. Org. Chem. 1978, 43, 353. (b) Alper, H.; Leonard, D. J. Chem. Soc., Chem. Commun. 1985, 511. (c) Chenal, T.; Naigre, R.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1993, 747. (d) Naigre, R.; Chenal, T.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Organomet. Chem. 1994, 480, 91. (d) Naigre, R.; Chenal, T.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Organomet. Chem. 1994, 480, 91.
169. For selected examples of metal-mediated carbonylation of unsaturated alcohols to lead to δ-lactones, see: (a) Murray, T. F.; Varma, V.; Norton, J. R. J. Org. Chem. 1978, 43, 353. (b) Alper, H.; Leonard, D. J. Chem. Soc., Chem. Commun. 1985, 511. (c) Chenal, T.; Naigre, R.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Chem. Soc., Chem. Commun. 1993, 747. (d) Naigre, R.; Chenal, T.; Ciprés, I.; Kalck, P.; Daran, J.-C.; Vaissermann, J. J. Organomet. Chem. 1994, 480, 91. (e) Chow, Y. L.; Huang, Y.-J.; Dragojlovic, V. Can. J. Chem. 1995, 73, 740. (e) Chow, Y. L.; Huang, Y.-J.; Dragojlovic, V. Can. J. Chem. 1995, 73, 740.
170. The general procedure for hydrogenation is given in the Supporting Information.
171. Fujiwara, Y.; Okamoto, M. Chem. Pharm. Bull. 1989, 37, 1458.
172. Pirkle, W. H.; Adams, P. E. J. Org. Chem. 1979, 44, 2169. Also see refs 20 and 21c and d.
173. (a) Carroll, F. I.; Mitchell, G. N.; Blackwell, J. T.; Sobti, A.; Meck, R. J. Org. Chem. 1974, 39, 3890.
174. (b) Pirkle, W. H.; Adams, P. E. J. Org. Chem. 1980, 45, 4117.