Singlet-oxygen generation in the catalytic reaction of dioxiranes with nucleophilic anions

Nucleophilic anions such as Cl-, I-, Br-, t-BuO-, O-2(-) and OH- efficiently catalyze the decomposition of dimethyldioxirane (DMD) and methyl(trifluoromethyl) dioxirane (TFD). Singlet oxygen (O-1(2)) is formed in these catalytic reactions, as demonstrated by the characteristic infrared chemiluminescence (IR-CL) at 1268 nm. The yield of O-1(2) generation, measured by the IR-CL method, lies in the range between 2 and 98%, which depends on the particular anion employed. For the bromide ion, the catalytic decomposition of the dioxirane is in competition with the oxidation of Br- to elemental bromine.