THE ISOMERIZATION/CHLORINATION OF O,O-DIALKYL N,N-DIALKYL THIOPHOSPHORAMIDATE WITH PHOSPHORUS OXYCHLORIDE—A NEW METHOD FOR SYNTHESIS OF S-ALKYL N,N-DIALKYL THIOPHOSPHORAMIDIC ACID DERIVATIVES

Abstract

A new convenient method for synthesis of S-alkyi N,N-dialkyl thiophosphoramidic acid derivatives is reported. The chlorination of O,O-dialkyl N,N-dialkyl thiophosphoramidates with phosphorus oxy-chloride proceeds with isomerization to give S-alkyl N,N-dialkyl thiophosphoramidochloridates, which react further with various nucleophilcs in the presence of base to give the title compounds. However, in the reaction of O,O-diethyl N,N-dimethyi thiophosphoramidate with phosphorus oxychloride, an unexpected exchange between chlorine atom and dimethylamino group is observed.

Key Words:

• Thiophosphoramidate
• thiophosphorochloridate
• isomerization
• chlorination