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

Article abstract of DOI:10.1016/0040-4039(96)01932-6

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.