How do reaction mechanisms change? Appearance of concerted pericyclic elimination for the reaction of cumyl derivatives

TL Amyes, JP Richard

Index: Amyes, Tina L.; Richard, John P. Journal of the American Chemical Society, 1991 , vol. 113, # 23 p. 8960 - 8961

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Citation Number: 15

Abstract

We report that destabilization of the carbocation intermediate of the stepwise solvolysis reaction of tertiary cumyl derivatives, XArC (Me), Y, by the addition of electron-withdrawing ring substituents, leads to a change in mechanism to concerted pericyclic elimination in which intramolecular proton transfer to the leaving group, Y= ArC02 or C1, is concerted with CY bond cleavage (see 1).