Aromatic triphenylmethylation

Add time:08/05/2019    Source:sciencedirect.com

The mechanism of homolytic triphenylmethylation of aromatic substrates has been studied by the reaction between diacyl peroxide and triphenylmethyl free radical in toluene, anisole and chlorobenzene. A previously proposed mechanism, involving acyloxycyclohexadienyl radical as intermediate, has been further ascertained by comparing relative reactivities of aromatic substrate in triphenylmethylation and the ratios meta to the sum of ortho and para substituted tetraphenylmethanes formed with relative reactivities of substrates in benzoyloxylation, isopropoxycarbonyloxylation and hydroxylation, and with the ratios of the sum of ortho and para to meta acyloxylation or hydroxylation products, respectively.

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