Reaction of phosphetan oxides with sulphonyl isocyanates and related reactions

Abstract

Phosphetan oxides (5) react with toluene-p-sulphonyl isocyanate (TsNCO) and chlorosulphuryl isocyanate (CSI) in a variety of solvents to give phosphetan imides [(6) or (7)] with retention of configuration. Phosphetans (8) can be converted into the corresponding imides (6) by using tosyl azide or TsNCO. also with retention of configuration. Alkaline hydrolysis of the imides (6) proceeds with no loss of chirality. The mechanisms of these reactions are discussed.