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

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. Copyright (C) 1996 Elsevier Science Ltd