Acid-catalyzed Rearrangement of the exo-1,2-Dioxetane Derivative from 1-Isopropylidene-4,4-diphenyl-2,5-cyclohexadiene

Article abstract of DOI:10.1246/bcsj.53.3279

It is shown that acid-catalyzed docomposition of the 1,2-dioxetane derivative, 3,3-dimethyl-7,7-diphenyl-1,2-dioxaspiro<3.5>nona-5,8-diene, obtained from 1-isopropylidene-4,4-diphenyl-2,5-cyclohexadiene, gives 1-methyl-1-(o-terphenyl-4'-yl)ethyl hydroperoxide, bis<1-methyl-1-(o-terphenyl-4'-yl)ethyl>peroxide, 1-(1-hydroperoxy-1-methylethyl)-4,4-diphenylcyclohexa-2,5-dien-1-ol, and o-terphenyl-4'-ol, along with the usual dioxetane-scission product, 4,4-diphenyl-2,5-cyclohexadienone.The distribution and yield of these products depend on acidic agents and/or conditions employed.