Singlet oxygen and electron-transfer mechanisms in the dicyanoanthracene-sensitized photooxidation of 2,3-diphenyl-1,4-dioxene

Article abstract of DOI:10.1021/ja00020a032

The 9,10-dicyanoanthracene-sensitized photooxidation of 2,3-diphenyl-1,4-dioxene in CH₃CN produces ethylene glycol dibenzoate and small amounts of epoxide. Most of the diester is formed from singlet oxygen via the dioxetane, and only a small amount by electron transfer. The epoxide is a primary electron-transfer product. Various mechanistic possibilites for the electron-transfer are considered.