Stereochemistry and reactivity in interconversions of three- and four-co-ordinate imino-derivatives of sulphur

Abstract

Optically pure sulphoxides have been converted into N-phthalimidosulphoximides by treatment with N-amino-phthalimide and lead tetra-acetate. Sulphoxides are regenerated in high yields and optical purities on treatment with sodium ethoxide or hydrazine in ethanol and it is suggested that each step in these two-step cycles occurs with retention of configuration at sulphur. No attack occurs at the carbon–carbon double bond in formation of the sulphoximide from p-tolyl vinyl sulphoxide.

Reactions of S-vinyl- and of S-β-substituted-ethyl-sulphimides have been briefly investigated in a qualitative evaluation of the activating effects of the sulphonylimino-sulphur group on elimination and addition reactions.