By H Suschitzky; O Meth-Cohn; Great Britain. The Royal Society of Chemistry
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Extra info for a review of the literature abstracted between July 1980 and June 1981
Sakai, Tetrahedron, 1979, 35,2861. R. Curci, M. Fiorentino, L. Troisi, J. 0. Edwards, and R. H. Pater, J. Org. , 1980,45,4758. F. Henin and J. P. Pete, Synthesis, 1980, 895. S. Torii, K. Uneyama, M. Ono, H. Tazawa, and S. , 1979,4661. -Predictions as to the reactivities and stabilities of oxirans continue to engage the interest of theoretical chemists. ]-derivatives, quantum and molecular mechanics have been used to show that cycloheptene oxide exists in a b ~ a t - c h a iand r ~ ~cyclohexene oxide in a half-chair'" conformation.
1, 1980,440. "' Using HC10, in THF, a 6p-OAc group completely blocked cleavage of both the a- and p-epoxides, and a 6a-OAc group retarded ring-opening compared with (130; R' = R2 = H). "~ The mechanism was found to be SN2-like, with all positional isomers that were formed in the AlC1,-catalysed reaction of epoxypropane having almost completely inverted configurations at the epoxide carbon. Cyclization Reactions of Oxirans. The three mono-epoxides of humulene (134) occur naturaliy, and may well serve as the precursors, in uiuo, of other bicyclic and tricyclic sesquiterpenoids that are of biological significance.
A m . Chem. , 1980, 102, 7725. S. Szakacs, S. Gobolos, and F. Nagy, Magy. Kem. , 1980, 86, 276 (Chem. , 1980, 93, '21 185 343). H. Kakiuchi and T. Iijima, Tetrahedron, 1980,36,101 1. 129In acid, the major reaction occurred at the benzilic carbon, C-2, with a large inverse isotope effect at C-3; however, in basic conditions, using methoxide, the situation was reversed, there being a large inverse isotope effect at C-2, with little effect at C-3. These results indicate that there is a large degree of ring-opening in both transition states.