THE 1,2-PHENYL MIGRATION OF DEPROTONATED BENZYLDIPHENYLAMINE IN THE GAS-PHASE

Deprotonated benzyldiphenylamine and its ring-substituted benzyl derivatives undergo the nitrogen analogue of the Wittig rearrangement in the gas phase to form deprotonated benzhydrylanilines as product anions. The analogous process occurs under base-catalysed conditions in the condensed phase. The collision-induced loss of benzene from the rearrangement ion is used as a probe for the rearrangement. It is proposed that this is a stepwise reaction in which the second step (the deprotonation of the CH position by the incipient phenyl anion) is rate-determining.