Oxathiirans. Part 5. Oxathiiran O-oxide, a possible intermediate in the reaction between singlet oxygen and thiocarbonyl compounds

Abstract

The reaction between thioformaldehyde and singlet oxygen has been investigated theoretically within a CNDO/B framework. Potential energy surface calculations predict a multistep mechanism involving primary formation of an oxathiiran O-oxide, which rearranges into a 1,2,3-dioxathietan system. Two possible rearrangement pathways are discussed. The four-membered ring is tentatively suggested to decompose via a biradicaloid intermediate.