Group transfer carbonylations: Photoinduced alkylative carbonylation of alkenes accompanied by phenylselenenyl transfer

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6396-6403

  Ryu, Ilhyong ^a   Muraoka, Hideo ^a   Kambe, Nobuaki ^a   Komatsu, Mitsuo ^a   Sonoda, Noboru ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000205932     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960349y     Document Type: Article

References (55)

1. For recent reviews, see: (a) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
2. For recent reviews, see: (a) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050. (b) Ryu, I.; Sonoda, N.; Curran, D. P. Chem. Rev. 1996, 96, 177.
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9. For kinetics, see: (c) Brown, C. E.; Neville, A. G.; Rayner, D. M.; Ingold, K. U.; Lusztyk, J. Aust. J. Chem. 1995, 48, 363.
10. Examples of recent applications to intramolecular alkene addition: (a) Lee, G. M.; Weinreb, S. M. J. Org. Chem. 1990, 55, 1281. (b) Pirrung, F. O. H.; Steeman, W. J. M.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B; Boesten, W. H. J.; Schoemaker, H. E.; Kamphuis, J. Tetrahedron Lett. 1992, 33, 5141. (c) Seijas, J. A.; Vázquez-Tato, M. P.; Castedo, L.; Estévez, R.; Ónega, M. G.; Ruíz, M. Tetrahedron 1992, 48, 1637. (d) Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464. (e) Ishibashi, H.; Uemura, N.; Nakatani, H.; Okazaki, M.; Tatsunori, S.; Nakamura, N.; Ikeda, M. J. Org. Chem. 1993, 58, 2360.
11. Examples of recent applications to intramolecular alkene addition: (a) Lee, G. M.; Weinreb, S. M. J. Org. Chem. 1990, 55, 1281. (b) Pirrung, F. O. H.; Steeman, W. J. M.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B; Boesten, W. H. J.; Schoemaker, H. E.; Kamphuis, J. Tetrahedron Lett. 1992, 33, 5141. (c) Seijas, J. A.; Vázquez-Tato, M. P.; Castedo, L.; Estévez, R.; Ónega, M. G.; Ruíz, M. Tetrahedron 1992, 48, 1637. (d) Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464. (e) Ishibashi, H.; Uemura, N.; Nakatani, H.; Okazaki, M.; Tatsunori, S.; Nakamura, N.; Ikeda, M. J. Org. Chem. 1993, 58, 2360.
12. Examples of recent applications to intramolecular alkene addition: (a) Lee, G. M.; Weinreb, S. M. J. Org. Chem. 1990, 55, 1281. (b) Pirrung, F. O. H.; Steeman, W. J. M.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B; Boesten, W. H. J.; Schoemaker, H. E.; Kamphuis, J. Tetrahedron Lett. 1992, 33, 5141. (c) Seijas, J. A.; Vázquez-Tato, M. P.; Castedo, L.; Estévez, R.; Ónega, M. G.; Ruíz, M. Tetrahedron 1992, 48, 1637. (d) Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464. (e) Ishibashi, H.; Uemura, N.; Nakatani, H.; Okazaki, M.; Tatsunori, S.; Nakamura, N.; Ikeda, M. J. Org. Chem. 1993, 58, 2360.
13. Examples of recent applications to intramolecular alkene addition: (a) Lee, G. M.; Weinreb, S. M. J. Org. Chem. 1990, 55, 1281. (b) Pirrung, F. O. H.; Steeman, W. J. M.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B; Boesten, W. H. J.; Schoemaker, H. E.; Kamphuis, J. Tetrahedron Lett. 1992, 33, 5141. (c) Seijas, J. A.; Vázquez-Tato, M. P.; Castedo, L.; Estévez, R.; Ónega, M. G.; Ruíz, M. Tetrahedron 1992, 48, 1637. (d) Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464. (e) Ishibashi, H.; Uemura, N.; Nakatani, H.; Okazaki, M.; Tatsunori, S.; Nakamura, N.; Ikeda, M. J. Org. Chem. 1993, 58, 2360.
14. Examples of recent applications to intramolecular alkene addition: (a) Lee, G. M.; Weinreb, S. M. J. Org. Chem. 1990, 55, 1281. (b) Pirrung, F. O. H.; Steeman, W. J. M.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B; Boesten, W. H. J.; Schoemaker, H. E.; Kamphuis, J. Tetrahedron Lett. 1992, 33, 5141. (c) Seijas, J. A.; Vázquez-Tato, M. P.; Castedo, L.; Estévez, R.; Ónega, M. G.; Ruíz, M. Tetrahedron 1992, 48, 1637. (d) Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464. (e) Ishibashi, H.; Uemura, N.; Nakatani, H.; Okazaki, M.; Tatsunori, S.; Nakamura, N.; Ikeda, M. J. Org. Chem. 1993, 58, 2360.
15. Phenylselenenyl group transfer to alkenes: (a) Byers, J. H.; Lane, G. C. Tetrahedron Lett. 1990, 31, 5697. (b) Byers, J. H.; Gleason. T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354. (c) Byers, J. H.; Harper, B. C. Tetrahedron Lett. 1992, 33, 6953. (d) Byers, J. H.; Lane, G. C. J. Org. Chem. 1993, 58, 3355. (e) Byers, J. H.; Thissell, J. G.; Thomas, M. A. Tetrahedron Lett. 1995, 36, 6403.
16. Phenylselenenyl group transfer to alkenes: (a) Byers, J. H.; Lane, G. C. Tetrahedron Lett. 1990, 31, 5697. (b) Byers, J. H.; Gleason. T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354. (c) Byers, J. H.; Harper, B. C. Tetrahedron Lett. 1992, 33, 6953. (d) Byers, J. H.; Lane, G. C. J. Org. Chem. 1993, 58, 3355. (e) Byers, J. H.; Thissell, J. G.; Thomas, M. A. Tetrahedron Lett. 1995, 36, 6403.
17. Phenylselenenyl group transfer to alkenes: (a) Byers, J. H.; Lane, G. C. Tetrahedron Lett. 1990, 31, 5697. (b) Byers, J. H.; Gleason. T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354. (c) Byers, J. H.; Harper, B. C. Tetrahedron Lett. 1992, 33, 6953. (d) Byers, J. H.; Lane, G. C. J. Org. Chem. 1993, 58, 3355. (e) Byers, J. H.; Thissell, J. G.; Thomas, M. A. Tetrahedron Lett. 1995, 36, 6403.
18. Phenylselenenyl group transfer to alkenes: (a) Byers, J. H.; Lane, G. C. Tetrahedron Lett. 1990, 31, 5697. (b) Byers, J. H.; Gleason. T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354. (c) Byers, J. H.; Harper, B. C. Tetrahedron Lett. 1992, 33, 6953. (d) Byers, J. H.; Lane, G. C. J. Org. Chem. 1993, 58, 3355. (e) Byers, J. H.; Thissell, J. G.; Thomas, M. A. Tetrahedron Lett. 1995, 36, 6403.
19. Phenylselenenyl group transfer to alkenes: (a) Byers, J. H.; Lane, G. C. Tetrahedron Lett. 1990, 31, 5697. (b) Byers, J. H.; Gleason. T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354. (c) Byers, J. H.; Harper, B. C. Tetrahedron Lett. 1992, 33, 6953. (d) Byers, J. H.; Lane, G. C. J. Org. Chem. 1993, 58, 3355. (e) Byers, J. H.; Thissell, J. G.; Thomas, M. A. Tetrahedron Lett. 1995, 36, 6403.
20. (a) Curran, D. P.; Thoma, G. J. Am. Chem. Soc. 1992, 114, 4436.
21. (b) Curran, D. P.; Eichenberger, E.; Collis, M.; Roepel, M. G.; Thoma, G. J. Am. Chem. Soc. 1994, 116, 4279.
22. (a) Han, L. B.; Ishihara, K.; Kambe, N.; Ogawa, A.; Ryu, I.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 7591.
23. (b) Vionnet, J. P.; Renaud, P. Helv. Chim. Acta 1994, 77, 1781.
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25. (d) Back, T. G.; Gladstone, P. L. Synlett 1993, 699.
26. (e) Renaud, P.; Abazi, S. Synthesis 1996, 253.
27. For rate constants for chalcogen group transfer, see: Curran, D. P.; Martin-Esker, A. A.; Ko, S.-B; Newcomb, M. J. Org. Chem. 1993, 58, 4691.
28. H2 process, see: (a) Chen, C.; Crich, D.; Papadatos, A. J. Am. Chem. Soc. 1992, 114, 8313. (b) Chen, C.; Crich, D. Tetrahedron Lett. 1993, 34, 1545. (c) Crich, D.; Chen, C.; Hwang, J.-T.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937.
29. H2 process, see: (a) Chen, C.; Crich, D.; Papadatos, A. J. Am. Chem. Soc. 1992, 114, 8313. (b) Chen, C.; Crich, D. Tetrahedron Lett. 1993, 34, 1545. (c) Crich, D.; Chen, C.; Hwang, J.-T.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937.
30. H2 process, see: (a) Chen, C.; Crich, D.; Papadatos, A. J. Am. Chem. Soc. 1992, 114, 8313. (b) Chen, C.; Crich, D. Tetrahedron Lett. 1993, 34, 1545. (c) Crich, D.; Chen, C.; Hwang, J.-T.; Yuan, H.; Papadatos, A.; Walter, R. I. J. Am. Chem. Soc. 1994, 116, 8937.
31. For radical polar effect of β-cyano substituent, see: Giese, B.; Engelbrecht, R. Polym. Bull. 1984, 12, 55.
32. Related work, see: (a) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (b) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett., in press.
33. Related work, see: (a) Ryu, I.; Kurihara, A.; Muraoka, H.; Tsunoi, S.; Kambe, N.; Sonoda, N. J. Org. Chem. 1994, 59, 7570. (b) Tsunoi, S.; Ryu, I.; Muraoka, H.; Tanaka, M.; Komatsu, M.; Sonoda, N. Tetrahedron Lett., in press.
34. Cf. ref 6d. For steric effects associated with radical additions, see: Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
35. The precise mechanism for the disproportionation is not clear yet, but we are now inclined to a possibility of elimination of PhSeH to give butyl acrylate and reduction of 1g by the resulting PhSeH to give butyl propionate. Cf.: Kropp, P. J.; Fryxell, G. E.; Tubergen, M. W.; Hager, M. W.; Harris, G. D., Jr.; McDermott, T. P., Jr.; Tornero-Verez, R. J. Am. Chem. Soc. 1991, 113, 7300.
36. The similar irradiation of 2-(phenylseleno)cyclohexanone resulted in the formation of cyclohexanone (35%) and 2-cyclohexenone (45%), but no alkene-addition products were detected with this substrate.
37. Diart, V.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 2 1992, 1761.
38. For kinetic effects on the cyclization of the radicals substituted by α-electron-withdrawing group, see: (a) Newcomb, M.; Filipkowski, M. A.; Johnson, C. C. Tetrahedron Lett. 1995, 36, 3643. (b) Newcomb, M.; Horner, J. H.; Filipkowski, M. A.; Ha, C.; Park, S.-U. J. Am. Chem. Soc. 1995, 117, 3674.
39. For kinetic effects on the cyclization of the radicals substituted by α-electron-withdrawing group, see: (a) Newcomb, M.; Filipkowski, M. A.; Johnson, C. C. Tetrahedron Lett. 1995, 36, 3643. (b) Newcomb, M.; Horner, J. H.; Filipkowski, M. A.; Ha, C.; Park, S.-U. J. Am. Chem. Soc. 1995, 117, 3674.
40. Under the photolytic conditions described in Scheme 2, 3b would not survive, if formed. In a separate experiment, photolysis of 3b took place to give 1b and diphenyl diselenide (4) as the main products ([3b] = 0.01 M, benzene, CO 80 atm, 44°C, 20 h).
41. Penn, J. H.; Liu, F. J. Org. Chem. 1994, 59, 2608.
42. Examples: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355, 4359. (c) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (d) Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759. (e) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821. (f) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. (h) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429. (i) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937. (j) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491. (k) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
43. Examples: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355, 4359. (c) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (d) Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759. (e) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821. (f) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. (h) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429. (i) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937. (j) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491. (k) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
44. Examples: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355, 4359. (c) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (d) Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759. (e) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821. (f) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. (h) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429. (i) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937. (j) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491. (k) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
45. Examples: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355, 4359. (c) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (d) Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759. (e) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821. (f) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. (h) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429. (i) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937. (j) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491. (k) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
46. Examples: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355, 4359. (c) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (d) Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759. (e) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821. (f) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. (h) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429. (i) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937. (j) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491. (k) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
47. Examples: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355, 4359. (c) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (d) Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759. (e) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821. (f) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. (h) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429. (i) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937. (j) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491. (k) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
48. Examples: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355, 4359. (c) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (d) Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759. (e) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821. (f) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. (h) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429. (i) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937. (j) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491. (k) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
49. Examples: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355, 4359. (c) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (d) Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759. (e) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821. (f) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. (h) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429. (i) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937. (j) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491. (k) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
50. Examples: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355, 4359. (c) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (d) Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759. (e) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821. (f) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. (h) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429. (i) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937. (j) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491. (k) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
51. Examples: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355, 4359. (c) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (d) Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759. (e) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821. (f) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. (h) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429. (i) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937. (j) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491. (k) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
52. Examples: (a) Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328. (b) Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355, 4359. (c) Ireland, R. E.; Norbeck, D. W.; Mandel, G. S.; Mandel, N. S. J. Am. Chem. Soc. 1985, 107, 3285. (d) Back, T. G.; Kerr, R. G. Tetrahedron 1985, 41, 4759. (e) Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821. (f) Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272. (g) Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. (h) Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1992, 57, 1429. (i) Kuniyasu, H.; Ogawa, A.; Higaki, K.; Sonoda, N. Organometallics 1992, 11, 3937. (j) Kuniyasu, H.; Ogawa, A.; Sonoda, N. Tetrahedron Lett. 1993, 34, 2491. (k) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
53. Cf. For carbocarboxylations of alkenes, see: Ryu, I.; Alper, H. J. Am. Chem. Soc. 1993, 115, 7543.
54. These compounds are already known, and the obtained spectroscopic data are in good agreement with those described in the following literature. (a) Toshimitsu, A.; Aoai, T.; Owada, H.; Uemura, S.; Okano, M. J. Chem. Soc., Chem. Commun. 1980, 412. (b) Detty, M. R.; Wood, G. P. J. Org. Chem. 1980, 45, 80.
55. These compounds are already known, and the obtained spectroscopic data are in good agreement with those described in the following literature. (a) Toshimitsu, A.; Aoai, T.; Owada, H.; Uemura, S.; Okano, M. J. Chem. Soc., Chem. Commun. 1980, 412. (b) Detty, M. R.; Wood, G. P. J. Org. Chem. 1980, 45, 80.