The Journal of Organic Chemistry

An efficient and remarkably regioselective synthesis of benzocyclobutenones from benzynes and 1, 1-dimethoxyethylene

RV Stevens, GS Bisacchi

Index: Stevens, Robert V.; Bisacchi, Gregory S. Journal of Organic Chemistry, 1982 , vol. 47, # 12 p. 2393 - 2396

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Citation Number: 84

Abstract

New efficient methodology for the synthesis of substituted benzocyclobutenones is presented that involves the [2+ 21 cycloaddition of various substituted benzynes to 1, l- dimethoxyethylene followed by hydrolysis to the corresponding ketone. In most cases studied a high degree of regioselectivity was observed. These observations are consistent with a nonsynchronous mechanism wherein steric and inductive considerations can be ...