Further demonstration of the higher reactivity of the vinyl hydrogen rather than the allyl hydrogen towards singlet oxygen

Abstract

In a new linear twisted 1,3-diene, an anomalously high reactivity of the vinyl hydrogen rather than the allyl hydrogen towards singlet oxygen is observed.

References

1. H. Mori, K. Ikoma, Y. Masui, S. Isoe, K. Kitaura and S. Katsumura, Tetrahedron Lett., 1996, 37, 7771.
2. D. Miller, M. Trammel, A. Kini and R. S. H. Liu, Tetrahedron Lett., 1981, 22, 409; G. Becher and A. Mannschreck, Chem. Ber., 1983, 116, 264; N. Sakai, J. Decatur and K. Nakanishi, J. Am. Chem. Soc., 1996, 118, 1559.
3. A. O. King, N. Okukado and E. Negishi, J. Chem. Soc., Chem. Commun., 1977, 683.
4. J. E. McMurry and W. J. Scott, Tetrahedron Lett., 1983, 24, 979.
5. J. E. Dubois, M. Boussu and C. Lion, Tetrahedron Lett., 1971, 829.
6. J. K. Stille and J. H. Simpson, J. Am. Chem. Soc., 1987, 109, 2138.
7. M. Orfanopoulos, M. Stratakis and Y. Elemes, J. Am. Chem. Soc., 1990, 112, 6417; W. Adam and J. Richer, Tetrahedron Lett., 1993, 34, 8423; M. Stratakis and M. Orfanopoulos, Tetrahedron Lett., 1995, 36, 4291.