Stereochemistry of the Thermal Isomerization of 1-Ethenyl-7-exo-Phenylbicyclo[4.1.0]heptane to 7-Phenylbicyclo[4.3.0]non-1(9)-ene: The Conformational Course of an Antarafacial,Retention Vinylcyclopropane-Cyclopentene Rearrangement

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4721-4725

  Baldwin, John E ^a   Bonacorsi Jr , Samuel J ^a,b   Burrell, Richard C ^a  

^a SYRACUSE UNIVERSITY   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000828034     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980420v     Document Type: Article

References (23)

1. For a synopsis of work on this rearrangement, and a listing of review articles, see Baldwin, J. E. J. Comput. Chem. 1998, 19, 222-231.
2. Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie: Weinheim, 1970; pp 121-122.
3. Willcott, M. R.; Cargle, V. H. J. Am. Chem. Soc. 1967, 89, 723-724.
4. Willcott, M. R.; Cargle, V. H. J. Am. Chem. Soc. 1969, 91, 4310-4311.
5. Baldwin, J. E. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, 1995; Vol. 2, pp 469-494.
6. Andrews, G. D.; Baldwin, J. E. J. Am. Chem. Soc. 1976, 98, 6705-6706.
7. Baldwin, J. E.; Ghatlia, N. D. J. Am. Chem. Soc. 1991, 113, 6273-6274.
8. Baldwin, J. E.; Bonacorsi, S. J. J. Am. Chem. Soc. 1993, 115, 10621-10627.
9. Baldwin, J. E.; Bonacorsi, S. J. J. Org. Chem. 1994, 59, 7401-7409.
10. Baldwin, J. E.; Villarica, K. A.; Freedberg, D. I.; Anet, F. A. L. J. Am. Chem. Soc. 1994, 116, 10845-10846.
11. Baldwin, J. E.; Villarica, K. A. J. Org. Chem. 1995, 60, 186-190.
12. Asuncion, L. A.; Baldwin, J. E. J. Org. Chem. 1995, 60, 5778-5784.
13. Asuncion, L. A.; Baldwin, J. E. J. Am. Chem. Soc. 1995, 117, 10672-10677 1995.
14. Baldwin, J. E.; Bonacorsi, S. J. J. Am. Chem. Soc. 1996, 118, 8258-8265.
15. Johnson, C. R.; Kirchhoff, R. A.; Reischer, R. J. J. Am. Chem. Soc. 1973, 95, 4287-4291.
16. Fringuelli, F.; Mancini, V.; Taticchi, A. Tetrahedron 1969, 25, 4249-4256.
17. Cristol, S. J.; Ilenda, C. S. J. Am. Chem. Soc. 1975, 97, 5862-5867.
18. Baldwin, J. E.; Bonacorsi, S. J. Abstracts of Papers, 213th National Meeting of the American Chemical Society, San Francisco, CA, April 13-17, 1997; American Chemical Society: Washington, DC, 1997; ORGN 265.
19. Davidson, E. R.; Gajewski, J. J. J. Am. Chem. Soc. 1997, 119, 10543-10544.
20. Houk, K. N.; Nendel, M.; Wiest, O.; Storer, J. W. J. Am. Chem. Soc. 1997, 119, 10545-10546.
21. Leonard, N. J.; Johnson, C. R. J. Org. Chem. 1962, 27, 282-284.
22. Shriner, R. L.; Struck, H. C.; Jorison, W. J. J. Am. Chem. Soc. 1930, 52, 2060-2069.
23. Doering, W. von E.; Depuy, C. H. J. Am. Chem. Soc. 1953, 75, 5954-5956.