Synthesis and Rearrangement of N-P^III-Phosphorylated Carboxylic Acid Amides

Abstract

Reactions of carboxylic acid lactams with tervalent phosphorus chlorides, leading to N- and/or O- derivatives have been investigated. Synthetic methods for imidoylphosphites and phosphonates, mono- and bisphosphorylated azadienes have been developed. Prototropic migrations in azaallylic triad, phosphorus atom migrations in N-C-O triad and imidoylphosphite-imidoylphosphonate rearrangement were found. It was encountered, that chlorination of amidophosphites containing one to three trihalogen acetamide groups is accompanied by chlorine or N-acylamide group shift and leads to cyclic and spirocyclic phosphoranes with 1,3,2-⁵-oxazaphosphetanic cycle.