Stereochemistry and Reactions of Aziridinylphosphinothionates Derived from Amino Acids

Abstract

Aziridinylphosphinothionates were prepared from optically active ethyl hydrogen phenylphosphonothionates and 1-bromo-2-alkanamines derived from leucine or valine. The aziridine ring was opened by the action of some nucleophiles. Refluxing the aziridinylphosphinothionates in acetone with sodium iodide caused hydrolysis accompanied by the rearrangement of the sulfur atom to give β-mercaptoethylphosphonamidates. The reaction mechanism was discussed with stereochemical considerations. The insecticidal activity of the products was also examined.