Site of attack of a carbene on alkylbenzenes, naphthalene, and thiophene and the norcaradiene-cycloheptatriene equilibration

CD Bedford, PAS Smith

Index: Bedford, Clifford D.; Smith, Peter A. S. Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4002 - 4010

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Citation Number: 4

Abstract

Upon thermolysis at 40-50" C, 5-(diazomethyl)-1, 4-diphenyl-1, 2, 3-triazole (1) reacts with p- ethyltoluene, p-cymene, p-tert-butyltoluene, p-diisopropylbenzene, durene, and naphthalene to give a mixture of carbene-derived cycloheptatriene/norcaradiene products; attack is favored adjacent to the more highly branched substituent. Decomposition of 1 in p- diisopropylbenzene afforded a tropilidene and a CH insertion product in a ca. 1: l ratio. ...