Use of carbohydrate derivatives for studies of phosphorus stereochemistry. Part III. Stereochemical course of nucleophilic displacements of 2-substituents in 1,3,2-dioxaphosphorinan-2-ones and related compounds

Abstract

The stereochemistry of displacement of 2-substituents from 1,3,2-dioxaphosphorinan-2-ones, 1,3,2-oxathiaphosphorinan-2-ones, and 1,3,2-dioxaphosphorinan-2-thiones has been shown to depend on the nature of both the entering and the leaving group. Inversion of configuration has been observed for reactions involving good leaving groups and weak nucleophiles whereas with less good leaving groups and stronger nucleophiles the displacement reactions proceed with retention of configuration.