Vinylidenes as Intermediates in Thermal Cyclopropene-to-Acetylene Rearrangements

Journal of the American Chemical Society

Volumn 116, Issue 14, 1994, Pages 6175-6178

  Likhotvorik, Igor R ^a   Jones, Maitland ^a   Brown, Duncan W ^b  

^a Advanced Technology Materials Inc   (United States)

^b PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001553497     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00093a016     Document Type: Article

References (25)

1. Liebman, J. F.; Greenberg, A. Strained Organic Molecules; Wiley: New York, 1978; pp 91-94.
2. Gajewski, J. J. Hydrocarbon Thermal Isomerizations; Wiley: New York, 1981; pp 22-25.
3. York, E. J.; Dittmar, W.; Stevenson, J. R.; Bergman, R. G. J. Am. Chem. Soc. 1972, 94, 2882; 1973, 95, 5680.
4. Yoshimine, M.; Pacansky, J.; Honjou, N. J. Am. Chem. Soc. 1989, 111, 2785, 4198.
5. Stang, P. J. In Carbene (oide); Regitz, M., Ed.; Georg Thieme: Stuttgart, 1989; p 84 ff.
6. Fahie, B. J.; Leigh, W. J. Can. J. Chem. 1989, 67, 1859.
7. Steinmetz, M. G. Org. Photochem. 1987, 8, 67. Kropp, P. J. Org. Photochem. 1979, 4, 1.
8. For a spectacular recent example of the use of this reaction see: Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082. For an archival example by the discoverer of the reaction see: Brown, R. F. C.; Harrington, K. J.; McMullen, G. L. J. Chem. Soc., Chem. Commun. 1974,123.
9. Chan, T. H.; Massuda, D. J. Am. Chem. Soc. 1977, 99, 936. Conlin, R. T.; Huffaker, H. B.; Kwak, Y.-W. J. Am. Chem. Soc. 1985, 107, 731. Barton, T. J.; Yeh, M.-H. Tetrahedron Lett. 1987, 28, 6421. Eaton, P. E.; Hoffmann, K.-L, J. Am. Chem. Soc. 1987, 109, 5285. Chen, N.; Jones, M., Jr.; White, W. R.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 4981.
10. Walsh, R.; Wolf, C; Untiedt, S.; de Meijere, A. J. Chem. Soc., Chem. Commun. 1992, 421.
11. Hopf, H.; Wachholz, G.; Walsh, R. Chem. Ber. 1985, 118, 3579.
12. Srinivasan, R. J. Chem. Soc., Chem. Commun. 1971, 1041.
13. Stang, P. J. Acc. Chem. Res. 1978, 11, 107.
14. Walsh, R.; Wolf, C; Untiedt, S.; de Meijere, A. J. Chem. Soc., Chem. Commun. 1992, 422.
15. Auner, N.; Walsh, R.; Westrup, C. J. Chem. Soc., Chem. Commun. 1986, 207.
16. Closs, G. L.; Closs, L. E. J. Am. Chem. Soc. 1963, 85, 99.
17. Stang, P. J. Private communication, December, 1993.
18. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
19. 13C-NMR-Specktroscopie; George Thieme: Stuttgart, 1984.
20. 1H FT NMR Spectra; Aldrich: Milwaukee, 1993; Vol. 1, p 38B.
21. Gross, H.; Gloede, J. Chem. Ber. 1963, 96, 1387.
22. Julia, S.; Ginebreda, A. Synthesis 1977, 682.
23. Baird, M. S.; Hussain, H. H.; Nethercroft, W. J. Chem. Soc., Perkin Trans. I 1986, 1845.
24. Nicholas, K. M.; Siegel, J. J. Am. Chem. Soc. 1985, 107, 4999.
25. Henry, L. Ber. Dtsch. Chem. Ges. 1875, 8, 398.