A novel approach for the formation of carbon-Nitrogen bonds: Azidation of alkyl radicals with sulfonyl azides

C Ollivier, P Renaud

Index: Ollivier; Renaud Journal of the American Chemical Society, 2001 , vol. 123, # 20 p. 4717 - 4727

Full Text: HTML

Citation Number: 95

Abstract

Two preparatively attractive methods for the azidation of alkyl radicals are described. Secondary and tertiary alkyl iodides and dithiocarbonates are easily converted into the corresponding azides, either by reaction with ethanesulfonyl azide in the presence of dilauroyl peroxide, or by treatment with benzenesulfonyl azide and hexabutylditin in the presence of a radical initiator. Interestingly, intramolecular tandem radical cyclization- ...