The stereochemistry of nucleophilic substitution at phosphorus in PIII and PV phosphetans

Abstract

Nucleophilic substitution of the chlorine atom in 1-chloro-2,2,3,4,4-pentamethylphosphetan occurs with inversion of configuration at phosphorus. Several stereochemical cycles based on this compound and involving phosphetan 1-oxides and 1-sulphides are described. They support the generalisation that nucleophilic substitution of electro-negative groups in phosphetan oxides and sulphides occurs with retention of configuration at phosphorus.