Stereochemistry of hydrolysis at an acyclic phosphoryl centre leading to an achiral phosphorus acid

Abstract

Alkaline hydrolysis of S_p-methyl methylphenylphosphinate in 60% H₂¹⁸O has been shown to involve predominant (>90%) inversion of configuration at phosphorus; esterification of the resulting acid with the diazocompounds (2) gave, inter alia, diastereoisomeric menthyl esters; the isotopic labelling of these was deduced from the ¹⁸O isotopic chemical shifts in their ³¹P n.m.r. spectra.