Singlet-oxygen generation in the catalytic reaction of dioxiranes with nucleophilic anions
Abstract
Nucleophilic anions such as Cl−, I−, Br−, t-BuO−, O2− and OH− efficiently catalyze the decomposition of dimethyldioxirane (DMD) and methyl(trifluoromethyl)dioxirane (TFD). Singlet oxygen (1O2) is formed in these catalytic reactions, as demonstrated by the characteristic infrared chemiluminescence (IR-CL) at 1268 nm. The yield of 1O2 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