Effect of allylic oxygen on the reaction pathways of singlet oxygenation: Selective formation of 1,2-dioxetanes from 1-alkoxymethyl-2-aryl-1-tert-butyl-2-methoxyethylenes

Article abstract of DOI:10.1016/0040-4039(95)02185-X

Olefins bearing an allylic oxygen 1 undergo 1,2-addition of singlet oxygen to afford exclusively the corresponding 1,2-dioxetanes 2, whereas their methylene analogues 3 suffer competitively 1,2-addition and ene reaction. The reactivity of 1 preferring 1,2-addition is likely attributed to the steering effect by an allylic oxygen.