Synthesis and Chemical Properties of Insecticidal 2-Alkoxy-4-alkyl-1, 3, 2-oxazaphospholidine 2-Sulfides Derived from Optically Active Amino Acids

Abstract

Some (4S)- and (4R)-2-alkoxy-4-alkyl-1, 3, 2-oxazaphospholidine 2-sulfides were prepared from optically active a-amino acids. They were mixtures of diasteromeric pairs, which were separated into isomers carefully by gas chromatography or thin-layer chromatography with multiple development technique. Their characteristics on NMR and mass fragmentation were determined in comparison with deuterium labeled compounds. Nucleophiles readily cleaved the five-membered ring by fission of the endocyclic P-O bond. In 2-chloro analog, however, a displacement reaction on the phosphorus occurred without a ring-opening.