Evidence for reversible ylide formation: Equilibrium between free alkylidenecarbenes and ethereal solvent-alkylidenecarbene complexes (oxonium ylides)

Journal of the American Chemical Society

Volumn 118, Issue 42, 1996, Pages 10141-10149

  Sueda, Takuya ^a   Nagaoka, Takema ^a   Goto, Satoru ^a   Ochiai, Masahito ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; QUANTUM CHEMISTRY; REACTION ANALYSIS;

EID: 0029855674     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961797q     Document Type: Article

References (104)

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49. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
50. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
51. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
52. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
53. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
54. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
55. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
56. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
57. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
58. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
59. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
60. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
61. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
62. For intramolecular 1,5-C-H insertion of alkylidenecarbenes, see: (a) Walsh, R. A.; Bottini, A. T. J. Org. Chem. 1970, 35, 1086. (b) Baumann, M.; Kobrich, G. Tetrahedron Lett. 1974, 1207. (c) Karpf, M.; Dreiding, A. S. Helv. Chim. Acta 1979, 62, 852. (d) Gilbert, J. C.; Giamalva, D. H.; Weerasooriya, U. J. Org. Chem. 1983, 48, 5251. (e) Gilbert, J. C.; Blackburn, B. K. Tetrahedron Lett. 1984, 25, 4067. (f) Gilbert, J. C.; Giamalva, D. H.; Baze, M. E. J. Org. Chem. 1985, 50, 2557. (g) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 3656. (h) Gilbert, J. C.; Blackburn, B. K. J. Org. Chem. 1986, 51, 4087. (i) Baird, M. S.; Baxter, A. G. W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc., Perkin Trans, 1 1991, 2575. (j) Ohira, S.; Okai, K.; Moritani, T. J. Chem. Soc., Chem. Commun. 1992, 721. (k) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (l) Kim, S.; Cho, C. M. Tetrahedron Lett. 1994, 35, 8405. (m) Williamson, B. L.; Tykwinski, R. R.; Stang, P. J. J. Am. Chem. Soc. 1994, 116, 93. (n) Tykwinski, R. R.; Stang, P. J.; Persky, N. E. Tetrahedron Leu. 1994, 35, 23. (o) Schildknegt, K.; Bohnstedt, A. C.; Feldman, K. S.; Sambandam, A. J. Am. Chem. Soc. 1995, 117, 7544.
63. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
64. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
65. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
66. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
67. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
68. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
69. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
70. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
71. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
72. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
73. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
74. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
75. For 1,2-shift of alkylidenecarbenes, see: (a) Bothner-By, A. A. J. Am. Chem. Soc. 1955, 77, 3293. (b) Wolinsky, J. J. Org. Chem. 1961, 26, 704. (c) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142. (d) Newman, M. S.; Gromelski, S. J. J. Org. Chem. 1972, 37, 3220. (e) Kobrich, G.; Merkel, D.; Thiem, K.-W. Chem. Ber. 1972, 105, 1683. (f) Wolinsky, J.; Clark, G. W.; Thorstenson, P. C. J. Org. Chem. 1976, 41, 745. (g) Kowalski, C. J.; Fields, K. W. J. Am. Chem. Soc. 1982, 104, 321. (h) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1982, 47, 1837. (i) McDougall, J. J. W.; Schlegel, H. B.; Francisco, J. S. J. Am. Chem. Soc. 1989, 111, 4622. (j) Walsh, R; Untiedt, S.; Stohlmeier, M.; Meijere, A. Chem. Ber. 1989, 122, 637. (k) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118. (l) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (m) Fischer, D. R.; Williamson, B. L.; Stang, P. J. Synlett 1992, 535.
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