Addition of Nitrogen Functionality to Exocyclic Alkenes: A New Procedure for Azidoselenenylation

Abstract

The reaction of exocyclic alkenes with N-phenylselenophthalimide and azidotrimethylsilane in dichloromethane affords ß-phenylselno azides. Products resulting from the elimination of either the azido or phenylseleno group are not observed under these conditions. Anti-Markovnikov regioselectivity is enhanced by the addition of tetrabutylammonium fluoride to the reaction.