The reactions of singlet oxygen with β-chlorosulfides. The role of hydroperoxy sulfonium ylides in the oxidative destruction of chemical warfare simulants

Article abstract of DOI:10.1016/S0040-4039(99)01304-0

The reactions of singlet oxygen with 2-chloroethyl ethyl sulfide and 3- chlorothiane are reported, In both cases elimination of HCl to produce α,β- unsaturated sulfoxides is observed. The experimental results implicate a hydroperoxy sulfonium ylide as a transition state or intermediate in an E2 or E1cb elimination, respectively.