Studies in mass spectrometry. Part XXVIII. Hydrogen scrambling between phenyl rings of diphenylmethanol and diphenylmethyl chloride

Abstract

It has been established from the mass spectra of deuteriated analogues of diphenylmethanol that partial hydrogen scrambling between phenyl rings occurs in the molecular ion of diphenylmethanol itself. Evidence is presented to support the hypothesis that the inter-ring scrambling occurs through reversible ring expansion to a cycloheptatriene structure. In the spectrum of diphenylmethyl chloride all the hydrogens in the (M– Cl) ion become equivalent prior to the expulsion of a methyl radical.