Tetrahedron letters

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

A Toutchkine, EL Clennan

Index: Toutchkine, Alexei; Clennan, Edward L. Tetrahedron Letters, 1999 , vol. 40, # 36 p. 6519 - 6522

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Citation Number: 14

Abstract

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 E1 cb elimination, respectively.

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