The reactions of t-butyl peroxide with toluene derivatives

Abstract

The reactions of t-butyl peroxide with toluene derivatives, containing chloro-, bromo-, cyano-, methyl-, and phenyl-substituents in the alkyl side chain and p-halogeno-substituents in the nucleus, give variable yields of the corresponding dehydro-dimers. Good yields are obtained with the p-halogeno-substituted cumenes, benzyl cyanide, p-chlorobenzyl cyanide, benzylidene dichloride, and p-bromoethylbenzene. α-Chloroethylbenzene, benzyl bromide, benzyl chloride, p-chlorobenzyl chloride, and p-tolunitrile give moderate to low yields of the expected dimers. However, p-bromobenzyl bromide, α-bromoethylbenzene, α-bromophenylacetonitrile, and diphenyl-bromomethane fail to dimerise in the expected manner. The available evidence in the case of diphenylchloromethane suggests that both hydrogen and chlorine are abstracted, giving rise to a variety of mixed products.