Regio-and diastereoselective formation of 1, 2-azidohydroperoxides by photooxygenation of alkenes in the presence of azide anions

AG Griesbeck, T Hundertmark, J Steinwascher

Index: Griesbeck, Axel G.; Hundertmark, Thomas; Steinwascher, Joerg Tetrahedron Letters, 1996 , vol. 37, # 46 p. 8367 - 8370

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Citation Number: 15

Abstract

1, 2-Azidohydroperoxides are accessible from alkenes when irradiated in the presence of azide anions, oxygen and an appropriate sensitizer. The results of substrate/sensitizer variations indicate a reaction initiated by electron transfer to give the sensitizer radical anion and azidyl radicals. The latter efficiently add to alkenes producing carbon radicals which are trapped by molecular oxygen.