Study of the Stability of O,O-Dialkyl-O-Arylthiophosphate: Evidence of the Formation of O,S-Dialkyl-O-Arylphosphate

GRAPHICAL ABSTRACT

Abstract

During the synthesis of cationic lipids that included thiophosphoramidate moiety or pincer ligands based on O,O-diethyl-thiophosphonate as coordination group, the rearrangement of O,O-diethyl-thiophosphoryl in O,S-diethylthiophosphoryl group was observed. This rearrangement, which does not occur by a simple heating at 130°C, is catalyzed by nucleophilic amine like N,N-dimethylaminopyridine. However, at some occasion, dealkylation of the O,S-diethylthiophosphoryl compound is observed.

Keywords:

• Rearrangement
• thiophosphonate
• organocatalysis