The Journal of Organic Chemistry

Homocyclic Ring Closures via Benzyne Intermediates. A New Synthesis of 1-Substituted Benzocyclobutenes1

JF Bunnett, JA Skorcz

Index: Bunnett,J.F.; Skorcz,J.A. Journal of Organic Chemistry, 1962 , vol. 27, p. 3836 - 3843

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Citation Number: 49

Abstract

Several aliphatic nitriles, esters, sulfones, and ketones bearing an wo-chlorophenyl substituent react with potassium amide in liquid ammonia to furnish cyclization products in which a homocyclic ring is fused into the benzene ring. Beneocyclobutene, indane, tetralin, and benzocycloheptene derivatives have been prepared, mostly in yields of 5&80%. Aryne intermediates are thought to be involved; this view is supported by the fact that both ortho- ...