Regioselectivity of the base??induced ring cleavage of 1??oxygenated derivatives of cyclobutabenzene

A Gokhale, P Schiess

Index: Gokhale, Abha; Schiess, Peter Helvetica Chimica Acta, 1998 , vol. 81, # 2 p. 251 - 267

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Citation Number: 22

Abstract

Abstract Oxy anions 3 generated from 1, 2-dihydrocyclobutabenzen-1-ones 1 through addition of a charged nucleophile or from 1-hydroxy-1, 2-dihydrocyclobutabenzenes 2 by deprotonation with base lead to stable products through distal and/or proximal cleavage of the strained four-membered ring via benzyl carbanion 4 and/or aryl carbanion 5. A systematic study of this process reveals the relative stability of the two isomeric carbanions ...