NOVEL N-(ALKYLTHIOMETHYL)IMINOPHOSPHORANES AND THEIR APPLICATION TO THE SYNTHESES OF NEW FUNCTIONALIZED N,S-ACETALS

Reaction of thiolates with (1-triphenylphosphorylideneaminomethyl)benzotriazole (betmip, 1) gave novel N-(alkylthiomethyl)iminophosphoranes 3 which were transformed, without isolation and in high yields, to N-(alkylthiomethyl)benzalimines 4, N-(alkyl)N'-(alkylthiomethyl)carbodiimides 5 and N-(alkylthiomethyl)amides 7 by treatment with araldehydes, tert-butyl isocyanate or acyl chlorides, respectively. N-(Alkylthiomethyl)-N'-tert-butylcarbodiimides 5 provide N-(alkyl)-N'-(alkylthiomethyl) ureas 6 in good yield.