Study of the Substituted Vinylallene-Methylenecyclobutene Electrocyclic Equilibria. Comparison with the Butadiene-Cyclobutene and Bisallene-Bismethylenecyclobutene Electrocyclic Equilibria

Journal of Organic Chemistry

Volumn 54, Issue 17, 1989, Pages 4028-4033

  Pasto, Daniel J ^a   Kong, Wei ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001693774     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00278a010     Document Type: Article

References (12)

1. Pasto, D. J.; Yang, S. H. J. Org. Chem., submitted for publication.
2. Pasto, D. J.; Yang, S. H. J. Org. Chem., submitted for publication.
3. Gil-Av, E.; Herling, R. Tetrahedron Lett. 1967, 1.
4. Pasto. D. J.: Kong, W. J. Ore. Chem. 1988. 53. 4807.
5. Frisch, M. J.; Binkley, J. S.; Schlegel, H. B.; Reghavachari, K.; Melius, C. F.; Martin, R. L.; Stewart, J. J. P.; Bobrowicz, F. W.; Rohlfing, C. C.; Kahn, L. R.; Defrees, D. J.; Seeger, R.; Whiteside, R. A.; Fox, D. J.; Fleuder, E. M.; Pople, J. A. Carnegie-Mellon Quantum Chemistry Publishing Unit. Pittsburgh. PA. 1984.
6. Traetteberg, M.; Bakken, P.; Hopf, H. Acta Chem. Scand. A 1980, 34, 461.
7. Lefevre, F.; Martin, M. L.; LeBail, H.; Odiot, S. Org. Magn. Reson. 1975, 7. 315.
8. Bischof, P.; Gleiter, R.; Hopf, H.; Lenich, F. T. J. Am. Chem. Soc. 1975, 97, 5467.
9. Benson, S. W. Thermochemical Kinetics. Methods for the Estimation of Thermochemical Data and Rate Parameters, 2nd ed.; John Wiley & Sons: New York, 1976.
10. Pasto, D. J.; Krasnansky, R.; Zercher, C. J. Org. Chem. 1987, 52, 3062.
11. Numerous examples of [l,5]-hydrogen sigmatropic rearrangements of substituted vinylallenes have been reported (Crowley, K. T. Proc. Chem. Soc. London 1964, 17. Minter, D. E.; Fonken, G. J.; Cook, F. T. Tetrahedron Lett. 1979, 711. Condran, P., Jr.; Okamura, W. H. J. Org. Chem. 1980, 45, 4015. Sueiras, J.; Okamura, W. H. J. Am. Chem. Soc. 1980,102, 6255. Haces, A.; Okamura, W. H. J. Am. Chem. Soc. 1982, 104, 6015. Condran, P.; Hammond, M. L.; Mourino, A.; Okamura, W. H. J. Am. Chem. Soc. 1980, 102, 6259).
12. Originally prepared by the base-catalyzed isomerization of 5-penten-l-yne (Grimaldi, J.; Bertrand, M. Bull. Soc. Chim. Fr. 1971, 947).