Cyclization Reactions of Rhodium Carbene Complexes. Effect of Composition and Oxidation State of the Metal

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1642-1652

  Padwa, Albert ^a   Kassir, Jamal M ^a   Xu, Simon L ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000936113     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962271r     Document Type: Article

References (90)

1. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; Mill Valley, CA, 1987.
2. Mass, G. Top. Curr. Chem. 1987, 137, 77.
3. Doyle, M. P. Acc. Chem. Res. 1986, 19, 348; Chem. Rev. 1986, 86, 919.
4. Doyle, M. P. Acc. Chem. Res. 1986, 19, 348; Chem. Rev. 1986, 86, 919.
5. Schore, N. E. Chem. Rev. 1988, 88, 1081.
6. Deem, M. L. Synthesis 1982, 701; 1972, 675.
7. Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. Dötz, K. H.; Popall, M. Tetrahedron 1985, 41, 5797. Dötz, K. H.; Dietz, R. Chem. Ber. 1978, 111, 2517.
8. Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. Dötz, K. H.; Popall, M. Tetrahedron 1985, 41, 5797. Dötz, K. H.; Dietz, R. Chem. Ber. 1978, 111, 2517.
9. Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1975, 14, 644. Dötz, K. H.; Popall, M. Tetrahedron 1985, 41, 5797. Dötz, K. H.; Dietz, R. Chem. Ber. 1978, 111, 2517.
10. Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5. Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc.: Greenwich, CT, 1989; Vol. 1. McCallum, J. S.; Kunng, F.-A.; Gilbertson, S. R.; Wulff, W. D. Organometallics 1988, 7, 2346. Wulff, W. D.; Xu, Y.-C. Tetrahedron Lett. 1988, 29, 415.
11. Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5. Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc.: Greenwich, CT, 1989; Vol. 1. McCallum, J. S.; Kunng, F.-A.; Gilbertson, S. R.; Wulff, W. D. Organometallics 1988, 7, 2346. Wulff, W. D.; Xu, Y.-C. Tetrahedron Lett. 1988, 29, 415.
12. Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5. Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc.: Greenwich, CT, 1989; Vol. 1. McCallum, J. S.; Kunng, F.-A.; Gilbertson, S. R.; Wulff, W. D. Organometallics 1988, 7, 2346. Wulff, W. D.; Xu, Y.-C. Tetrahedron Lett. 1988, 29, 415.
13. Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1990; Vol. 5. Wulff, W. D. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press Inc.: Greenwich, CT, 1989; Vol. 1. McCallum, J. S.; Kunng, F.-A.; Gilbertson, S. R.; Wulff, W. D. Organometallics 1988, 7, 2346. Wulff, W. D.; Xu, Y.-C. Tetrahedron Lett. 1988, 29, 415.
14. Peterson, G. A.; Kunng, F.-A.; McCallum, J. S.; Wulff, W. D. Tetrahedron Lett. 1987, 28, 1381.
15. Semmelhack, M. F.; Bozell, J. J.; Keller, L.; Sato, T.; Spiess, E. J.; Wu, W.; Zask, A. Tetrahedron 1985, 41, 5803.
16. Burkhardt, E. R.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2022.
17. Alt, H. G. J. Organomet. Chem. 1985, 288, 149.
18. Watson, P. L.; Bergman, R. G. J. Am. Chem. Soc. 1979, 101, 2055.
19. Slough, G. A.; Deshong, P. J. Am. Chem. Soc. 1988, 110, 2575.
20. Davidson, J. L.; Green, M.; Stone, F. G. A.; Welch, A. J. J. Chem. Soc., Dalton Trans. 1976, 2044.
21. Bottrill, M.; Green, M.; O'Brien, E.; Smart, L. E.; Woodward, P. J. Chem. Soc., Dalton Trans. 1980, 292.
22. Corrigan, P. A.; Dickson, R. S. Aust. J. Chem. 1979, 32, 2147.
23. Huggins, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 3002.
24. Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93.
25. O'Connor, J. M.; Pu, L.; Rheingold, A. L. J. Am. Chem. Soc. 1990, 112, 6232.
26. Harvey, D. F.; Brown, M. F. J. Am. Chem. Soc. 1990, 112, 7806. Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 5066. Harvey, D. F.; Brown, M. F. J. Org. Chem. 1992, 57, 5559. Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271.
27. Harvey, D. F.; Brown, M. F. J. Am. Chem. Soc. 1990, 112, 7806. Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 5066. Harvey, D. F.; Brown, M. F. J. Org. Chem. 1992, 57, 5559. Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271.
28. Harvey, D. F.; Brown, M. F. J. Am. Chem. Soc. 1990, 112, 7806. Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 5066. Harvey, D. F.; Brown, M. F. J. Org. Chem. 1992, 57, 5559. Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271.
29. Harvey, D. F.; Brown, M. F. J. Am. Chem. Soc. 1990, 112, 7806. Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 5066. Harvey, D. F.; Brown, M. F. J. Org. Chem. 1992, 57, 5559. Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271.
30. Grubbs, R. H. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Able, E. W., Eds.; Pergamon: New York, 1982; Vol. 8, p 499.
31. Dragutan, V.; Balaban, A. T.; Dimonie, M. Olefin Metathesis and Ring-Opening Polymerization of Cyclo-Olefins, 2nd ed.; Wiley-Interscience: New York, 1985.
32. Brookhart, M.; Studabaker, W. B. Chem. Rev. 1987, 87, 411.
33. Casey, C. P. In Reactive Intermediates; Jones, M., Moss, R. A., Eds.; Wiley: New York, 1981; p 135.
34. Dötz, K. H. Angew Chem., Int. Ed. Engl. 1984, 23, 587; Tetrahedron Symposia in Print; Semmelhack, M. F., Ed. 1986, 42, 5741-5887.
35. Dötz, K. H. Angew Chem., Int. Ed. Engl. 1984, 23, 587; Tetrahedron Symposia in Print; Semmelhack, M. F., Ed. 1986, 42, 5741-5887.
36. Padwa, A.; Krumpe, K. E.; Zhi, L. Tetrahedron Lett. 1989, 2623. Padwa, A.; Chiacchio, U.; Gareau, Y.; Kassir, J. M.; Krumpe, K. E.; Schoffstall, A. M. J. Org. Chem. 1990, 55, 414. Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. J. Org. Chem. 1991, 56, 2523. Kinder, F. R.; Padwa, A. Tetrahedron Lett. 1990, 31, 6835. Padwa, A.; Krumpe, K. E.; Kassir, J. M. J. Org. Chem. 1992, 57, 4940. Padwa, A.; Austin, D. J.; Xu, S. L. Tetrahedron Lett. 1991, 32, 4103. Padwa, A.; Gareau, Y.; Xu, S. L. Tetrahedron Lett. 1991, 32, 983.
37. Padwa, A.; Krumpe, K. E.; Zhi, L. Tetrahedron Lett. 1989, 2623. Padwa, A.; Chiacchio, U.; Gareau, Y.; Kassir, J. M.; Krumpe, K. E.; Schoffstall, A. M. J. Org. Chem. 1990, 55, 414. Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. J. Org. Chem. 1991, 56, 2523. Kinder, F. R.; Padwa, A. Tetrahedron Lett. 1990, 31, 6835. Padwa, A.; Krumpe, K. E.; Kassir, J. M. J. Org. Chem. 1992, 57, 4940. Padwa, A.; Austin, D. J.; Xu, S. L. Tetrahedron Lett. 1991, 32, 4103. Padwa, A.; Gareau, Y.; Xu, S. L. Tetrahedron Lett. 1991, 32, 983.
38. Padwa, A.; Krumpe, K. E.; Zhi, L. Tetrahedron Lett. 1989, 2623. Padwa, A.; Chiacchio, U.; Gareau, Y.; Kassir, J. M.; Krumpe, K. E.; Schoffstall, A. M. J. Org. Chem. 1990, 55, 414. Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. J. Org. Chem. 1991, 56, 2523. Kinder, F. R.; Padwa, A. Tetrahedron Lett. 1990, 31, 6835. Padwa, A.; Krumpe, K. E.; Kassir, J. M. J. Org. Chem. 1992, 57, 4940. Padwa, A.; Austin, D. J.; Xu, S. L. Tetrahedron Lett. 1991, 32, 4103. Padwa, A.; Gareau, Y.; Xu, S. L. Tetrahedron Lett. 1991, 32, 983.
39. Padwa, A.; Krumpe, K. E.; Zhi, L. Tetrahedron Lett. 1989, 2623. Padwa, A.; Chiacchio, U.; Gareau, Y.; Kassir, J. M.; Krumpe, K. E.; Schoffstall, A. M. J. Org. Chem. 1990, 55, 414. Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. J. Org. Chem. 1991, 56, 2523. Kinder, F. R.; Padwa, A. Tetrahedron Lett. 1990, 31, 6835. Padwa, A.; Krumpe, K. E.; Kassir, J. M. J. Org. Chem. 1992, 57, 4940. Padwa, A.; Austin, D. J.; Xu, S. L. Tetrahedron Lett. 1991, 32, 4103. Padwa, A.; Gareau, Y.; Xu, S. L. Tetrahedron Lett. 1991, 32, 983.
40. Padwa, A.; Krumpe, K. E.; Zhi, L. Tetrahedron Lett. 1989, 2623. Padwa, A.; Chiacchio, U.; Gareau, Y.; Kassir, J. M.; Krumpe, K. E.; Schoffstall, A. M. J. Org. Chem. 1990, 55, 414. Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. J. Org. Chem. 1991, 56, 2523. Kinder, F. R.; Padwa, A. Tetrahedron Lett. 1990, 31, 6835. Padwa, A.; Krumpe, K. E.; Kassir, J. M. J. Org. Chem. 1992, 57, 4940. Padwa, A.; Austin, D. J.; Xu, S. L. Tetrahedron Lett. 1991, 32, 4103. Padwa, A.; Gareau, Y.; Xu, S. L. Tetrahedron Lett. 1991, 32, 983.
41. Padwa, A.; Krumpe, K. E.; Zhi, L. Tetrahedron Lett. 1989, 2623. Padwa, A.; Chiacchio, U.; Gareau, Y.; Kassir, J. M.; Krumpe, K. E.; Schoffstall, A. M. J. Org. Chem. 1990, 55, 414. Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. J. Org. Chem. 1991, 56, 2523. Kinder, F. R.; Padwa, A. Tetrahedron Lett. 1990, 31, 6835. Padwa, A.; Krumpe, K. E.; Kassir, J. M. J. Org. Chem. 1992, 57, 4940. Padwa, A.; Austin, D. J.; Xu, S. L. Tetrahedron Lett. 1991, 32, 4103. Padwa, A.; Gareau, Y.; Xu, S. L. Tetrahedron Lett. 1991, 32, 983.
42. Padwa, A.; Krumpe, K. E.; Zhi, L. Tetrahedron Lett. 1989, 2623. Padwa, A.; Chiacchio, U.; Gareau, Y.; Kassir, J. M.; Krumpe, K. E.; Schoffstall, A. M. J. Org. Chem. 1990, 55, 414. Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. J. Org. Chem. 1991, 56, 2523. Kinder, F. R.; Padwa, A. Tetrahedron Lett. 1990, 31, 6835. Padwa, A.; Krumpe, K. E.; Kassir, J. M. J. Org. Chem. 1992, 57, 4940. Padwa, A.; Austin, D. J.; Xu, S. L. Tetrahedron Lett. 1991, 32, 4103. Padwa, A.; Gareau, Y.; Xu, S. L. Tetrahedron Lett. 1991, 32, 983.
43. Hoye, T. R.; Dinsmore, C. J.; Johnson, D. S.; Korkowski, P. F. J. Org. Chem. 1990, 55, 4518. Hoye, T. R.; Dinsmore, C. J. J. Am. Chem. Soc. 1991, 113, 4343. Hoye, T. R.; Dinsmore, C. J. Tetrahedron Lett. 1991, 32, 3755. Hoye, T. R.; Dinsmore, C. J. Tetrahedron Lett. 1992, 33, 169.
44. Hoye, T. R.; Dinsmore, C. J.; Johnson, D. S.; Korkowski, P. F. J. Org. Chem. 1990, 55, 4518. Hoye, T. R.; Dinsmore, C. J. J. Am. Chem. Soc. 1991, 113, 4343. Hoye, T. R.; Dinsmore, C. J. Tetrahedron Lett. 1991, 32, 3755. Hoye, T. R.; Dinsmore, C. J. Tetrahedron Lett. 1992, 33, 169.
45. Hoye, T. R.; Dinsmore, C. J.; Johnson, D. S.; Korkowski, P. F. J. Org. Chem. 1990, 55, 4518. Hoye, T. R.; Dinsmore, C. J. J. Am. Chem. Soc. 1991, 113, 4343. Hoye, T. R.; Dinsmore, C. J. Tetrahedron Lett. 1991, 32, 3755. Hoye, T. R.; Dinsmore, C. J. Tetrahedron Lett. 1992, 33, 169.
46. Hoye, T. R.; Dinsmore, C. J.; Johnson, D. S.; Korkowski, P. F. J. Org. Chem. 1990, 55, 4518. Hoye, T. R.; Dinsmore, C. J. J. Am. Chem. Soc. 1991, 113, 4343. Hoye, T. R.; Dinsmore, C. J. Tetrahedron Lett. 1991, 32, 3755. Hoye, T. R.; Dinsmore, C. J. Tetrahedron Lett. 1992, 33, 169.
47. Padwa, A.; Austin, D. J.; Xu, S. L. J. Org. Chem. 1992, 57, 1330. Padwa, A.; Xu, S. L. J. Am. Chem. Soc. 1992, 114, 5881.
48. Padwa, A.; Austin, D. J.; Xu, S. L. J. Org. Chem. 1992, 57, 1330. Padwa, A.; Xu, S. L. J. Am. Chem. Soc. 1992, 114, 5881.
49. The authors have deposited coordinates for structures 8 and 9 with the Cambridge Data Centre. The coordinates can be obtained from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
50. Wiberg, K. B.; Artis, D. R.; Bonneville, G. J. Am. Chem. Soc. 1991, 113, 7969.
51. Billups, W. E.; Lee, G. A.; Arney, B. E.; Whitmire, K. H. J. Am. Chem. Soc. 1991, 113, 7980.
52. One of the reviewers has suggested an alternate mechanism for the conversion of 20/22 into 14 which involves rearrangement of a cyclized alkyl carbenoid (i.e., A) to a vinyl-Rh-H intermediate B followed by chemical equations presented reductive elimination. However, this proposal does not account for why the change in solvent type causes the difference in reaction pathway. For other examples of product control of a rhodium-catalyzed process being influenced by solvent, see: Davies, H. M. L.; Saikali, E.; Clark, T. J.; Chee, E. H. Tetrahedron Lett. 1990, 31, 6299. Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440. Davies, H. M. L.; Hu, B.; Saikali, E.; Bruzinski, P. R. J. Org. Chem. 1994, 59, 4535.
53. One of the reviewers has suggested an alternate mechanism for the conversion of 20/22 into 14 which involves rearrangement of a cyclized alkyl carbenoid (i.e., A) to a vinyl-Rh-H intermediate B followed by chemical equations presented reductive elimination. However, this proposal does not account for why the change in solvent type causes the difference in reaction pathway. For other examples of product control of a rhodium-catalyzed process being influenced by solvent, see: Davies, H. M. L.; Saikali, E.; Clark, T. J.; Chee, E. H. Tetrahedron Lett. 1990, 31, 6299. Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440. Davies, H. M. L.; Hu, B.; Saikali, E.; Bruzinski, P. R. J. Org. Chem. 1994, 59, 4535.
54. One of the reviewers has suggested an alternate mechanism for the conversion of 20/22 into 14 which involves rearrangement of a cyclized alkyl carbenoid (i.e., A) to a vinyl-Rh-H intermediate B followed by chemical equations presented reductive elimination. However, this proposal does not account for why the change in solvent type causes the difference in reaction pathway. For other examples of product control of a rhodium-catalyzed process being influenced by solvent, see: Davies, H. M. L.; Saikali, E.; Clark, T. J.; Chee, E. H. Tetrahedron Lett. 1990, 31, 6299. Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440. Davies, H. M. L.; Hu, B.; Saikali, E.; Bruzinski, P. R. J. Org. Chem. 1994, 59, 4535.
55. One of the reviewers has suggested an alternate mechanism for the conversion of 20/22 into 14 which involves rearrangement of a cyclized alkyl carbenoid (i.e., A) to a vinyl-Rh-H intermediate B followed by chemical equations presented reductive elimination. However, this proposal does not account for why the change in solvent type causes the difference in reaction pathway. For other examples of product control of a rhodium-catalyzed process being influenced by solvent, see: Davies, H. M. L.; Saikali, E.; Clark, T. J.; Chee, E. H. Tetrahedron Lett. 1990, 31, 6299. Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696. Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440. Davies, H. M. L.; Hu, B.; Saikali, E.; Bruzinski, P. R. J. Org. Chem. 1994, 59, 4535.
56. Davies, H. M. L.; Romines, K. R. Tetrahedron 1988, 44, 3343.
57. Müller, P.; Pautex, N.; Doyle, M. P.; Bagheri, V. Helv. Chim. Acta 1990, 73, 1233. Müller, P.; Gränicher Helv. Chim. Acta 1993, 76, 521. Müller, P.; Gränicher Helv. Chim. Acta 1995, 78, 129.
58. Müller, P.; Pautex, N.; Doyle, M. P.; Bagheri, V. Helv. Chim. Acta 1990, 73, 1233. Müller, P.; Gränicher Helv. Chim. Acta 1993, 76, 521. Müller, P.; Gränicher Helv. Chim. Acta 1995, 78, 129.
59. Müller, P.; Pautex, N.; Doyle, M. P.; Bagheri, V. Helv. Chim. Acta 1990, 73, 1233. Müller, P.; Gränicher Helv. Chim. Acta 1993, 76, 521. Müller, P.; Gränicher Helv. Chim. Acta 1995, 78, 129.
60. Bishop, K. C. Chem. Rev. 1976, 76, 461.
61. Davies, H. M. L.; Clark, D. M.; Alligood, D. B.; Eiband, G. R. Tetrahedron 1987, 4265.
62. York, E. J.; Dittmar, W.; Stevenson, R. J.; Bergman, R. J. Am. Chem. Soc. 1973, 95, 5680; 1972, 94, 2882.
63. York, E. J.; Dittmar, W.; Stevenson, R. J.; Bergman, R. J. Am. Chem. Soc. 1973, 95, 5680; 1972, 94, 2882.
64. Al-Dulayyami, J.; Baird, M. S.; Clegg, W. Tetrahedron Lett. 1988, 29, 6149.
65. Padwa, A.; Fryxell, G. E. Advances in Strain in Organic Chemistry; Halton, B., Ed.; JAI Press: 1991; Vol. 1.
66. Pincock, J. A.; Moutsakapas, A. A. Can. J. Chem. 1977, 55, 979.
67. Binger, P.; Buch, H. M. Top. Curr. Chem. 1987, 135, 77.
68. Baird, M. S. Top. Curr. Chem. 1988, 144, 137.
69. Halton, B.; Banwell, M. G. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Patai, S., Eds.; John Wiley: New York, 1987; pp 1223-1339.
70. Binger, P.; Müller, P.; Benn, R.; Mynott, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 610. Binger, P.; Müller, P.; Hermann, A. T.; Phillips, P.; Gabor, B.; Langhau, F. Chem. Ber. 1991, 124, 2165.
71. Binger, P.; Müller, P.; Benn, R.; Mynott, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 610. Binger, P.; Müller, P.; Hermann, A. T.; Phillips, P.; Gabor, B.; Langhau, F. Chem. Ber. 1991, 124, 2165.
72. Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 8130.
73. Fredericks, S.; Thomas, J. L. J. Am. Chem. Soc. 1978, 100, 350.
74. Fischer, H.; Hofmann, J.; Mauz, E. Angew. Chem., Int. Ed. Engl. 1991, 30, 998.
75. Klimes, J.; Weiss, E. Angew. Chem., Int. Ed. Engl. 1982, 21, 205. Klimes, J.; Weiss, E. Chem. Ber. 1982, 115, 2606. Valeri, T.; Meier, F.; Weiss, E. Chem. Ber. 1988, 121, 1093.
76. Klimes, J.; Weiss, E. Angew. Chem., Int. Ed. Engl. 1982, 21, 205. Klimes, J.; Weiss, E. Chem. Ber. 1982, 115, 2606. Valeri, T.; Meier, F.; Weiss, E. Chem. Ber. 1988, 121, 1093.
77. Klimes, J.; Weiss, E. Angew. Chem., Int. Ed. Engl. 1982, 21, 205. Klimes, J.; Weiss, E. Chem. Ber. 1982, 115, 2606. Valeri, T.; Meier, F.; Weiss, E. Chem. Ber. 1988, 121, 1093.
78. Hughes, R. P.; MacKenzie, E. K.; Robinson, D. J.; Spotts, J. M. J. Am. Chem. Soc. 1989, 111, 8919. Hermond, R. C.; Hughes, R. P.; Robinson, D. J.; Rheingold, A. L. Organometallics 1988, 7, 2239.
79. Hughes, R. P.; MacKenzie, E. K.; Robinson, D. J.; Spotts, J. M. J. Am. Chem. Soc. 1989, 111, 8919. Hermond, R. C.; Hughes, R. P.; Robinson, D. J.; Rheingold, A. L. Organometallics 1988, 7, 2239.
80. Li, R. T.; Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 10032.
81. Tebbe, F. N.; Harlow, R. L. J. Am. Chem. Soc. 1980, 102, 6151.
82. Cho, S. K.; Liebeskind, L. S. J. Org. Chem. 1987, 52, 2633.
83. Salomon, R. G.; Salomon, M. F.; Kachinski, J. L. C. J. Am. Chem. Soc. 1977, 99, 1043.
84. Sarel, S. Acc. Chem. Res. 1978, 11, 204.
85. Daly, J. W.; Jerina, D. M.; Witkop, B. Experientia 1972, 28, 1129.
86. Boyd, D. R. Chem. Heterocycl. Compd. 1985, 42, 197.
87. Vinylketenes bearing unsaturated substituents at C-4 are known to cyclize to phenols; see: Danheiser, R. L.; Brisbois, R. G.; Kowalczyk, J. J.; Miller, R. F. J. Am. Chem. Soc. 1990, 112, 3093. Krysan, D. K.; Gurski, A.; Liebeskind, L. S. J. Am. Chem. Soc. 1992, 114, 1412. Perri, S. T.; Moore, H. W. J. Am. Chem. Soc. 1990, 113, 1897.
88. Vinylketenes bearing unsaturated substituents at C-4 are known to cyclize to phenols; see: Danheiser, R. L.; Brisbois, R. G.; Kowalczyk, J. J.; Miller, R. F. J. Am. Chem. Soc. 1990, 112, 3093. Krysan, D. K.; Gurski, A.; Liebeskind, L. S. J. Am. Chem. Soc. 1992, 114, 1412. Perri, S. T.; Moore, H. W. J. Am. Chem. Soc. 1990, 113, 1897.
89. Vinylketenes bearing unsaturated substituents at C-4 are known to cyclize to phenols; see: Danheiser, R. L.; Brisbois, R. G.; Kowalczyk, J. J.; Miller, R. F. J. Am. Chem. Soc. 1990, 112, 3093. Krysan, D. K.; Gurski, A.; Liebeskind, L. S. J. Am. Chem. Soc. 1992, 114, 1412. Perri, S. T.; Moore, H. W. J. Am. Chem. Soc. 1990, 113, 1897.
90. Allen, A. D.; Tidwell, T. T. Tetrahedron Lett. 1991, 32, 847.