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

Deprotonated benzyldiphenylamine and its ring-substituted benzyl deriv atives undergo the nitrogen analogue of the Wittig rearrangement in th e gas phase to form deprotonated benzhydrylanilines as product anions. The analogous process occurs under base-catalysed conditions in the c ondensed phase. The collision-induced loss of benzene from the rearran gement ion is used as a probe for the rearrangement. It is proposed th at this is a stepwise reaction in which the second step (the deprotona tion of the CH position by the incipient phenyl anion) is rate-determi ning.