The Mechanism of the Base-Promoted Rearrangement of N,N-Dichlorodiphenylethylamine to Desylamine

N,N-Dichloro -1,2-diphenylethylamine-1- 14C has been treated with sodium methoxide in methanol and then with hydrochloric acid to yield 14C-labeled desylamine hydrochloride Successive degradations have revealed that practically all the 14C activity was found in the carbonyl carbon. From the 14C distribution, it has been concluded that the reaction is essentially the same as that proposed for the Neber rearrangement, which involves the formation of the azirine ring intermediate.