AUTOXIDATION OF ADAMANTYLIDENEADAMANTANE IN A PROTIC SOLVENT. FACILE PROTON-INDUCED ELECTRON TRANSFER FROM THE OLEFIN TO OXYGEN

Article abstract of DOI:10.1016/S0040-4039(00)99966-0

Addition of trifluoroacetic acid to adamantylideneadamantane in dichloromethane solution under oxygen in the dark results in a rapid oxygenation of the olefin.The reaction is proposed to proceed through a mechanism involving proton-induced electon transfer from the olefin to oxygen giving its radical cation and a hydroperoxy radical followed by their subsequent reactions.