M. Inoue, Y. Taguchi, T. Sugita
Jun 1, 1979
Citations
0
Influential Citations
3
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The temperature effects on the stereochemistry of the acid-catalyzed ethanolysis of trans-2,3-diphenyloxirane were examined. The stereochemistry of the reaction became more retentive as the reaction temperature was raised. The reaction mechanisms are discussed, and it is concluded that concurrent reactions take place in the ethanolysis, one of them giving an inverted product, and the other, a retained one, and that the former reaction is caused by a nucleophilic attack of ethanol on the carbon of the conjugate acid of the epoxide, while the latter proceeds via an intermediate which has a carbonium-ion character.