The efficient synthesis of 1,2-dioxetanes from indene and 1,2-dihydronaphthalene

Indene (1), 1-methylindene (7), 2-methylindene (10), 1,2- and 1,4-dihydrona phthalenes (3 and 18) were converted into their trans-1,2-bromohydroperoxid es. The latter on treatment with a mixture of Ag2O/AgOSO2CF3 in CH2Cl2 at r oom temperature gave the corresponding 1,2-dioxetanes in yields of 90, 88, 80, 80, and 50% respectively. The cis-disposed bromo-hydroperoxide obtained from 7 was unreactive on treatment with the silver mixture. Similar treatm ent of the trans-bromo-hydroperoxide obtained from 33-dimethylindene (14) w as equally without effect, no dioxetane being formed.