Reaction of a triazolylcarbene with the xylenes and mesitylene and the resulting norcaradiene-tropilidene rearrangements

CD Bedford, EM Bruckmann…

Index: Bedford, C. D.; Bruckmann, E. M.; Smith, P. A. S. Journal of Organic Chemistry, 1981 , vol. 46, # 4 p. 679 - 686

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Citation Number: 5

Abstract

An improved synthesis of 5-(diazomethyl)-1, 4-diphenyl-1, 2, 3-triazole (1) has been developed. It fragments to a carbene at 40-50 “C and reacts with 0-, m-, or p-xylene or indan at 40-50 OC to give high yields of cycloheptatriene products, presumably through an initial norcaradiene adduct. In each case only one major isomer was obtained, indicating that steric interactions are a more important influence on the site selectivity of carbene attack ...

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