Issue 7, 1983

Oxidation of diphenylmethanol by bromamine T. A kinetic and mechanistic study

Abstract

Bromamine T (BAT) oxidises diphenylmethanol and substituted diphenylmethanols smoothly and quantitatively to the respective benzophenones in aquoeus acetic acid. Mineral acids catalyse the reaction and the rate law is found to be –d[BAT]/dt=k[BAT][Alcohol][H+]. The reaction is characterised by the absence of any kinetic isotope effect and a break in the Hammett plot with ρ values of –4.2 and –0.4 for the two limbs. Three alternative mechanistic pathways have been proposed involving (i) diphenylmethyl cation, (ii) a ‘phenonium ion’ type intermediate from the decomposition of the alkyl hypobromite ester, or (iii)ipso substitution at the benzene ring followed by dehydrobromination and aromatization.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1983, 949-953

Oxidation of diphenylmethanol by bromamine T. A kinetic and mechanistic study

S. Gunasekaran and N. Venkatasubramanian, J. Chem. Soc., Perkin Trans. 2, 1983, 949 DOI: 10.1039/P29830000949

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