Rearrangements of tolylmethylenes via cycloheptatetraenes: formation of benzocyclobutene and styrene

OL Chapman, RJ McMahon…

Index: Chapman, Orville L.; McMahon, Robert J.; West, Paul R. Journal of the American Chemical Society, 1984 , vol. 106, # 25 p. 7973 - 7974

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Citation Number: 32

Abstract

The thermolysis of 0-, m-, and p-tolyldiazomethanes to styrene and benzocyclobutene poses a mechanism problem of substantial interest. Several intriguing solutions to this problem have been suggested, 14 and labeling st~ dies,',~*~ have placed severe mechanistic constraints on possible solutions. Our studies on the phenylmethylene-cycloheptatetraene interconver~ ion~ prompted an investigation of the tolylmethylene rearrangement. We now ...