Photoinduced electron transfer reactions of alkenes and azide anions in the presence of molecular oxygen: Formation and chemistry of 1,2-azidohydroperoxides

A synthetic protocol has been developed that allows the chemo-, regio- and diastereoselective addition of azidyl radicals and molecular oxygen to elec tron-donor as well as electron-acceptor substituted acyclic and cyclic alke nes to give 1,2-azidohydroperoxides. These compounds were easily reducible to give 1,2-azidoalcohols and subsequently 1,2-aminoalcohols. The azidohydr operoxide from beta -pinene is the first example which could be characteriz ed by X-ray structure analysis.