Abstract
A series of O-( o- and p-azido)benzyl thiocarbamates smoothly rearranged in the course of Staudinger imination reactions with tertiary phosphines, giving rise to the respective S-( o- and p-phosphinimino)benzyl thiocarbamates as a result of an oxygen to sulfur migration of the functionalized benzyl group. By contrary, their m-azido isomers did not rearrange under similar conditions. Computational investigations using DFT methods revealed the uncoupled concerted mechanisms of these 1,3-benzyl shifts via polar transition states with pseudopericyclic orbital topologies, with the benzyl group migrating in the plane of the thiocarbamate fragment.
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