Radical-chain reactions of sulfonyl azides and of ethyl azidoformate with allylstannanes: homolytic allylation at nitrogen

HS Dang, BP Roberts

Index: Dang, Hai-Shan; Roberts, Brian P. Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 13 p. 1493 - 1498

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Abstract

4-Methylbenzenesulfonyl azide reacts with allyltriphenylstannane (ATPS) in refluxing benzene, in the presence of 2, 2′-azobis (2-methylpropionitrile) as initiator, to give N-allyl-4- methylbenzenesulfonamide in good yield after hydrolytic work-up. Small amounts of allyl 4- methylphenyl sulfone were also formed. The reaction follows a free-radical chain mechanism which involves competitive addition of Ph3Sn˙ to Na and to Nc of the azido ...