Preparation of Vinylcyclopropanes by the Titanocene-Promoted Reactions of β,γ-Unsaturated Thioacetals and Their Analogues with Alkenes

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3678-3682

  Horikawa, Yasuo ^a   Nomura, Tadahiro ^a   Watanabe, Mikako ^a   Fujiwara, Tooru ^a   Takeda, Takeshi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001154907     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962265v     Document Type: Article

References (53)

1. (a) Takeda, T.; Ando, K.; Mamada, A.; Fujiwara, T. Chem. Lett. 1985, 1149.
2. (b) Takeda, T.; Oshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345.
3. Takeda, T.; Ogawa, S.; Ohta, N.; Fujiwara, T. Chem. Lett. 1987, 1967.
4. Yamaguchi, J.; Tamada, Y.; Takeda, T. Bull. Chem. Soc. Jpn. 1993, 66, 607.
5. Takeda, T.; Miura, I.; Horikawa, Y.; Fujiwara, T. Tetrahedron Lett. 1995, 36, 1495.
6. Furuta, K.; Ikeda, Y.; Meguriya, N.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2781.
7. Ito, H.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 1992, 33, 7873.
8. Reviews: (a) Goldschmidt, Z.; Crammer, B. Chem. Soc. Rev. 1988, 17, 229. (b) Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1989, 33, 247. (c) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 899. (d) Khusnutdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1.
9. Reviews: (a) Goldschmidt, Z.; Crammer, B. Chem. Soc. Rev. 1988, 17, 229. (b) Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1989, 33, 247. (c) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 899. (d) Khusnutdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1.
10. Reviews: (a) Goldschmidt, Z.; Crammer, B. Chem. Soc. Rev. 1988, 17, 229. (b) Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1989, 33, 247. (c) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 899. (d) Khusnutdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1.
11. Reviews: (a) Goldschmidt, Z.; Crammer, B. Chem. Soc. Rev. 1988, 17, 229. (b) Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. 1989, 33, 247. (c) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 899. (d) Khusnutdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1.
12. For the transformation to cyclopentenes, see: (a) McGaffin, G.; de Meijere, A.; Walsh, R. Chem. Ber. 1991, 124, 939. (b) Davies, H. M. L.; Hu, B. Tetrahedron Lett. 1992, 33, 453. (c) Dolbier, W. R., Jr.; McClinton, M. A. J. Fluorine Chem. 1995, 70, 249. (d) Asuncion, L. A.; Baldwin, J. E. J. Org. Chem. 1995, 60, 5778. (e) Gajewski, J. J.; Olson, L. P.; Willcott, M. R., III. J. Am. Chem. Soc. 1996, 118, 299.
13. For the transformation to cyclopentenes, see: (a) McGaffin, G.; de Meijere, A.; Walsh, R. Chem. Ber. 1991, 124, 939. (b) Davies, H. M. L.; Hu, B. Tetrahedron Lett. 1992, 33, 453. (c) Dolbier, W. R., Jr.; McClinton, M. A. J. Fluorine Chem. 1995, 70, 249. (d) Asuncion, L. A.; Baldwin, J. E. J. Org. Chem. 1995, 60, 5778. (e) Gajewski, J. J.; Olson, L. P.; Willcott, M. R., III. J. Am. Chem. Soc. 1996, 118, 299.
14. For the transformation to cyclopentenes, see: (a) McGaffin, G.; de Meijere, A.; Walsh, R. Chem. Ber. 1991, 124, 939. (b) Davies, H. M. L.; Hu, B. Tetrahedron Lett. 1992, 33, 453. (c) Dolbier, W. R., Jr.; McClinton, M. A. J. Fluorine Chem. 1995, 70, 249. (d) Asuncion, L. A.; Baldwin, J. E. J. Org. Chem. 1995, 60, 5778. (e) Gajewski, J. J.; Olson, L. P.; Willcott, M. R., III. J. Am. Chem. Soc. 1996, 118, 299.
15. For the transformation to cyclopentenes, see: (a) McGaffin, G.; de Meijere, A.; Walsh, R. Chem. Ber. 1991, 124, 939. (b) Davies, H. M. L.; Hu, B. Tetrahedron Lett. 1992, 33, 453. (c) Dolbier, W. R., Jr.; McClinton, M. A. J. Fluorine Chem. 1995, 70, 249. (d) Asuncion, L. A.; Baldwin, J. E. J. Org. Chem. 1995, 60, 5778. (e) Gajewski, J. J.; Olson, L. P.; Willcott, M. R., III. J. Am. Chem. Soc. 1996, 118, 299.
16. For the transformation to cyclopentenes, see: (a) McGaffin, G.; de Meijere, A.; Walsh, R. Chem. Ber. 1991, 124, 939. (b) Davies, H. M. L.; Hu, B. Tetrahedron Lett. 1992, 33, 453. (c) Dolbier, W. R., Jr.; McClinton, M. A. J. Fluorine Chem. 1995, 70, 249. (d) Asuncion, L. A.; Baldwin, J. E. J. Org. Chem. 1995, 60, 5778. (e) Gajewski, J. J.; Olson, L. P.; Willcott, M. R., III. J. Am. Chem. Soc. 1996, 118, 299.
17. For the transformation to dienes, see: (a) Parziale, P. A.; Berson, J. A. J. Am. Chem. Soc. 1991, 113, 4595. (b) Ogle, C. A.; Black, K. C.; Sims, P. F. J. Org. Chem. 1992, 57, 3499. (c) Hanzawa, Y.; Harada, S.; Nishio, R.; Taguchi, T. Tetrahedron Lett. 1994, 35, 9421. (d) Dimmock, P. W.; Whitby, R. J. J. Chem. Soc., Chem. Commun. 1994, 2323.
18. For the transformation to dienes, see: (a) Parziale, P. A.; Berson, J. A. J. Am. Chem. Soc. 1991, 113, 4595. (b) Ogle, C. A.; Black, K. C.; Sims, P. F. J. Org. Chem. 1992, 57, 3499. (c) Hanzawa, Y.; Harada, S.; Nishio, R.; Taguchi, T. Tetrahedron Lett. 1994, 35, 9421. (d) Dimmock, P. W.; Whitby, R. J. J. Chem. Soc., Chem. Commun. 1994, 2323.
19. For the transformation to dienes, see: (a) Parziale, P. A.; Berson, J. A. J. Am. Chem. Soc. 1991, 113, 4595. (b) Ogle, C. A.; Black, K. C.; Sims, P. F. J. Org. Chem. 1992, 57, 3499. (c) Hanzawa, Y.; Harada, S.; Nishio, R.; Taguchi, T. Tetrahedron Lett. 1994, 35, 9421. (d) Dimmock, P. W.; Whitby, R. J. J. Chem. Soc., Chem. Commun. 1994, 2323.
20. For the transformation to dienes, see: (a) Parziale, P. A.; Berson, J. A. J. Am. Chem. Soc. 1991, 113, 4595. (b) Ogle, C. A.; Black, K. C.; Sims, P. F. J. Org. Chem. 1992, 57, 3499. (c) Hanzawa, Y.; Harada, S.; Nishio, R.; Taguchi, T. Tetrahedron Lett. 1994, 35, 9421. (d) Dimmock, P. W.; Whitby, R. J. J. Chem. Soc., Chem. Commun. 1994, 2323.
21. For the divinylcyclopropane-cycloheptadiene rearrangement, see: (1) Hudlicky, T.; Fan, R.; Reed, J. W.; Gadamasetti, K. G. Org. React. 1992, 41, 1. (b) Erbes, P.; Boland, W. Helv. Chim. Acta 1992, 75, 766.
22. For the divinylcyclopropane-cycloheptadiene rearrangement, see: (1) Hudlicky, T.; Fan, R.; Reed, J. W.; Gadamasetti, K. G. Org. React. 1992, 41, 1. (b) Erbes, P.; Boland, W. Helv. Chim. Acta 1992, 75, 766.
23. For example: (a) Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 8916. (b) de Meijere, A.; Schulz, T.-J.; Kostikov, R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547. (c) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441. (d) Shavrin, K. N.; Okonnishnikova, G. P.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2552; Chem. Abstr. 1992, 116, 83002q. (e) Weng, W.-W.; Luh, T.-Y. J. Chem. Soc., Perkin Trans. 1 1993, 2687. (f) Al Dulayymi, J. R.; Baird, M. S.; Rajaram, L.; Clegg, W. J. Chem. Res. (S) 1994, 344. (g) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247. For synthesis by the reaction of ruthenium-vinylcarbene complex with styrene, see: Nishiyama, H.; Park, S.-B.; Itoh, K. Chem. Lett. 1995, 599.
24. For example: (a) Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 8916. (b) de Meijere, A.; Schulz, T.-J.; Kostikov, R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547. (c) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441. (d) Shavrin, K. N.; Okonnishnikova, G. P.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2552; Chem. Abstr. 1992, 116, 83002q. (e) Weng, W.-W.; Luh, T.-Y. J. Chem. Soc., Perkin Trans. 1 1993, 2687. (f) Al Dulayymi, J. R.; Baird, M. S.; Rajaram, L.; Clegg, W. J. Chem. Res. (S) 1994, 344. (g) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247. For synthesis by the reaction of ruthenium-vinylcarbene complex with styrene, see: Nishiyama, H.; Park, S.-B.; Itoh, K. Chem. Lett. 1995, 599.
25. For example: (a) Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 8916. (b) de Meijere, A.; Schulz, T.-J.; Kostikov, R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547. (c) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441. (d) Shavrin, K. N.; Okonnishnikova, G. P.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2552; Chem. Abstr. 1992, 116, 83002q. (e) Weng, W.-W.; Luh, T.-Y. J. Chem. Soc., Perkin Trans. 1 1993, 2687. (f) Al Dulayymi, J. R.; Baird, M. S.; Rajaram, L.; Clegg, W. J. Chem. Res. (S) 1994, 344. (g) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247. For synthesis by the reaction of ruthenium-vinylcarbene complex with styrene, see: Nishiyama, H.; Park, S.-B.; Itoh, K. Chem. Lett. 1995, 599.
26. For example: (a) Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 8916. (b) de Meijere, A.; Schulz, T.-J.; Kostikov, R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547. (c) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441. (d) Shavrin, K. N.; Okonnishnikova, G. P.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2552; Chem. Abstr. 1992, 116, 83002q. (e) Weng, W.-W.; Luh, T.-Y. J. Chem. Soc., Perkin Trans. 1 1993, 2687. (f) Al Dulayymi, J. R.; Baird, M. S.; Rajaram, L.; Clegg, W. J. Chem. Res. (S) 1994, 344. (g) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247. For synthesis by the reaction of ruthenium-vinylcarbene complex with styrene, see: Nishiyama, H.; Park, S.-B.; Itoh, K. Chem. Lett. 1995, 599.
27. For example: (a) Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 8916. (b) de Meijere, A.; Schulz, T.-J.; Kostikov, R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547. (c) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441. (d) Shavrin, K. N.; Okonnishnikova, G. P.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2552; Chem. Abstr. 1992, 116, 83002q. (e) Weng, W.-W.; Luh, T.-Y. J. Chem. Soc., Perkin Trans. 1 1993, 2687. (f) Al Dulayymi, J. R.; Baird, M. S.; Rajaram, L.; Clegg, W. J. Chem. Res. (S) 1994, 344. (g) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247. For synthesis by the reaction of ruthenium-vinylcarbene complex with styrene, see: Nishiyama, H.; Park, S.-B.; Itoh, K. Chem. Lett. 1995, 599.
28. For example: (a) Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 8916. (b) de Meijere, A.; Schulz, T.-J.; Kostikov, R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547. (c) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441. (d) Shavrin, K. N.; Okonnishnikova, G. P.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2552; Chem. Abstr. 1992, 116, 83002q. (e) Weng, W.-W.; Luh, T.-Y. J. Chem. Soc., Perkin Trans. 1 1993, 2687. (f) Al Dulayymi, J. R.; Baird, M. S.; Rajaram, L.; Clegg, W. J. Chem. Res. (S) 1994, 344. (g) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247. For synthesis by the reaction of ruthenium-vinylcarbene complex with styrene, see: Nishiyama, H.; Park, S.-B.; Itoh, K. Chem. Lett. 1995, 599.
29. For example: (a) Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 8916. (b) de Meijere, A.; Schulz, T.-J.; Kostikov, R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547. (c) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441. (d) Shavrin, K. N.; Okonnishnikova, G. P.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2552; Chem. Abstr. 1992, 116, 83002q. (e) Weng, W.-W.; Luh, T.-Y. J. Chem. Soc., Perkin Trans. 1 1993, 2687. (f) Al Dulayymi, J. R.; Baird, M. S.; Rajaram, L.; Clegg, W. J. Chem. Res. (S) 1994, 344. (g) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247. For synthesis by the reaction of ruthenium-vinylcarbene complex with styrene, see: Nishiyama, H.; Park, S.-B.; Itoh, K. Chem. Lett. 1995, 599.
30. For example: (a) Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 8916. (b) de Meijere, A.; Schulz, T.-J.; Kostikov, R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547. (c) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441. (d) Shavrin, K. N.; Okonnishnikova, G. P.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2552; Chem. Abstr. 1992, 116, 83002q. (e) Weng, W.-W.; Luh, T.-Y. J. Chem. Soc., Perkin Trans. 1 1993, 2687. (f) Al Dulayymi, J. R.; Baird, M. S.; Rajaram, L.; Clegg, W. J. Chem. Res. (S) 1994, 344. (g) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247. For synthesis by the reaction of ruthenium-vinylcarbene complex with styrene, see: Nishiyama, H.; Park, S.-B.; Itoh, K. Chem. Lett. 1995, 599.
31. For example: (a) Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 8916. (b) de Meijere, A.; Schulz, T.-J.; Kostikov, R. R.; Graupner, F.; Murr, T.; Bielfeldt, T. Synthesis 1991, 547. (c) Taber, D. F.; Hoerrner, R. S. J. Org. Chem. 1992, 57, 441. (d) Shavrin, K. N.; Okonnishnikova, G. P.; Nefedov, O. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1991, 2552; Chem. Abstr. 1992, 116, 83002q. (e) Weng, W.-W.; Luh, T.-Y. J. Chem. Soc., Perkin Trans. 1 1993, 2687. (f) Al Dulayymi, J. R.; Baird, M. S.; Rajaram, L.; Clegg, W. J. Chem. Res. (S) 1994, 344. (g) Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247. For synthesis by the reaction of ruthenium-vinylcarbene complex with styrene, see: Nishiyama, H.; Park, S.-B.; Itoh, K. Chem. Lett. 1995, 599.
32. For example: (a) Feldman, K. S.; Simpson, R. E. J. Am. Chem. Soc. 1989, 111, 4878. (b) Parziale, P. A.; Berson, J. A. J. Am. Chem. Soc. 1991, 113, 4595. (c) Baldwin, J. E.; Bonacorsi, S., Jr. J. Org. Chem. 1994, 59, 7401. (d) Yamazaki, S.; Tanaka, M.; Yamaguchi, A.; Yamabe, S. J. Am. Chem. Soc. 1994, 116, 2356.
33. For example: (a) Feldman, K. S.; Simpson, R. E. J. Am. Chem. Soc. 1989, 111, 4878. (b) Parziale, P. A.; Berson, J. A. J. Am. Chem. Soc. 1991, 113, 4595. (c) Baldwin, J. E.; Bonacorsi, S., Jr. J. Org. Chem. 1994, 59, 7401. (d) Yamazaki, S.; Tanaka, M.; Yamaguchi, A.; Yamabe, S. J. Am. Chem. Soc. 1994, 116, 2356.
34. For example: (a) Feldman, K. S.; Simpson, R. E. J. Am. Chem. Soc. 1989, 111, 4878. (b) Parziale, P. A.; Berson, J. A. J. Am. Chem. Soc. 1991, 113, 4595. (c) Baldwin, J. E.; Bonacorsi, S., Jr. J. Org. Chem. 1994, 59, 7401. (d) Yamazaki, S.; Tanaka, M.; Yamaguchi, A.; Yamabe, S. J. Am. Chem. Soc. 1994, 116, 2356.
35. For example: (a) Feldman, K. S.; Simpson, R. E. J. Am. Chem. Soc. 1989, 111, 4878. (b) Parziale, P. A.; Berson, J. A. J. Am. Chem. Soc. 1991, 113, 4595. (c) Baldwin, J. E.; Bonacorsi, S., Jr. J. Org. Chem. 1994, 59, 7401. (d) Yamazaki, S.; Tanaka, M.; Yamaguchi, A.; Yamabe, S. J. Am. Chem. Soc. 1994, 116, 2356.
36. (a) Luh, T.-Y.; Wong, C. S. J. Org. Chem. 1985, 50, 5413.
37. (b) Yeung, L. L.; Yip, Y. C.; Luh, T.-Y. J. Chem. Soc., Chem. Commun. 1987, 981.
38. Wong, C. S.; Leung, W. S.; Yeung, L. L.; Luh, T.-Y. J. Organomet. Chem. 1986, 307, C49.
39. Ng, D. K. P.; Luh, T.-Y. Tetrahedron Lett. 1988, 29, 5131.
40. (e) Wang, X.-J.; Luh, T.-Y. J. Org. Chem. 1989, 54, 263.
41. (f) Yeung, L. L.; Yip, Y. C.; Luh, T.-Y. J. Org. Chem. 1990, 55, 1874.
42. (g) Tip, Y. C.; Wang, X.-J.; Ng, D. K. P.; Mak, T. C. W.; Chiang, P.; Luh, T.-Y. J. Org. Chem. 1990, 55, 1881.
43. (h) Kuo, C.-H.; Luh, T.-Y. J. Chem. Soc., Chem. Commun. 1990, 1187.
44. Preliminary communication: Horikawa, Y.; Nomura, T.; Watanabe, M.; Miura, I.; Fujiwara, T.; Takeda, T. Tetrahedron Lett. 1995, 36, 8835.
45. McDermott, J. X.; Wilson, M. E.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6529.
46. b: (a) Chang, M.; Timms, P. L.; King, R. B. J. Organomet. Chem. 1980, 199, C3. (b) Kool, L. B.; Raush, M. D.; Alt, H. G.; Herberhold, M.; Thewalt, U.; Wolf, B. Angew. Chem., Int. Ed. Engl. 1985, 24, 394.
47. b: (a) Chang, M.; Timms, P. L.; King, R. B. J. Organomet. Chem. 1980, 199, C3. (b) Kool, L. B.; Raush, M. D.; Alt, H. G.; Herberhold, M.; Thewalt, U.; Wolf, B. Angew. Chem., Int. Ed. Engl. 1985, 24, 394.
48. Horikawa, Y.; Watanabe, M.; Fujiwara, T.; Takeda, T. J. Am. Chem. Soc. 1997, 119, 1127.
49. c have been prepared using 3,3-disubstituted cyclopropenes as starting materials: (a) Binger, P.; Müller, P.; Benn, R.; Mynott, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 610. (b) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 3974. (c) Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 8130.
50. c have been prepared using 3,3-disubstituted cyclopropenes as starting materials: (a) Binger, P.; Müller, P.; Benn, R.; Mynott, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 610. (b) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 3974. (c) Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 8130.
51. c have been prepared using 3,3-disubstituted cyclopropenes as starting materials: (a) Binger, P.; Müller, P.; Benn, R.; Mynott, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 610. (b) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 3974. (c) Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 8130.
52. Ni, Z.-J.; Luh, T.-Y. Org. Synth. 1991, 70, 240.
53. Corey, E. J.; Erickson, B. W.; Noyori, R. J. Am. Chem. Soc. 1971, 93, 1724.