Characterization of two chloro-substituted m-benzyne isomers: effect of substitution on reaction efficiencies and products

The studies were conducted to generate two chloro-substituted isomers of m-benzyne and the effect of the chloro-substituent on the reactivity and relative stability of the isomers was investigated. The results state that all of the N-phenylpyridinium m-benzyne ions reacted with tert-butye isocyanide to form a strained, cyclic allene that was 70 k cal/mol less stable than one of its hydrogen-shift isomers.