Facile One-Pot Synthesis and X-ray Characterization of N-(Thio)phosphoryl-2-oxo-1,2-azaphospholanes: First Example of Cyclic O,O- and O,S-Bidentate Ligands with the P-N-P Backbone

Abstract

A convenient one-pot synthesis of N-phosphoryl-and Nthiophosphoryl-2-oxo-1,2-azaphospholanes was developed, starting from commercially available or simple-to-prepare phosphorus(III) acid chlorides and (3-bromopropyl)amine hydrobromide. The method is based on the intramolecular Arbuzov reaction of bisphosphorus(III)-substituted N-(3-bromopropyl)amines generated in turn by double phosphorylation of (3-bromopropyl)amine, followed by oxidation or sulfur addition to the cyclic phosphorus(III) species formed.