Organic Letters 2003-09-04

Ritter-type reactions of N-chlorosaccharin: a method for the electrophilic diamination of alkenes.

Kevin I Booker-Milburn, Dominic J Guly, Brian Cox, Panayiotis A Procopiou

Index: Org. Lett. 5(18) , 3313-5, (2003)

Full Text: HTML

Abstract

[reaction: see text] N-Chlorosaccharin has been shown to undergo electrophilic Ritter-type reactions with alkenes in acetonitrile. The resulting labile beta-chloro sulfonylamidines can be ring-opened and cyclized to imidazolines. Overall this provides a one pot method for the electrophilic diamination of alkenes. Competing aziridine formation as well as allylic chlorination are also observed depending on the nature of the alkene used.