Azidosulfonylation of alkenes, dienes, and enynes

The radical mediated aziclosulfonylation of various alkenes and alkynes that are able to undergo a rapid radical rearrangement is reported. For instance, treatment of 1,6-dienes or 1-en-6-ynes with benzenesulfonyl azide affords cyclic azidosulfones. High yields are observed when tertiary alkyl radicals are azidated in the last step of the cascade process. The aziclosulfonylation of P-pinene involving ring opening of the bicyclic skeleton is also reported. (C) 2008 Elsevier Ltd. All rights reserved.