Some chemistry of phenylsulfoxyacetic acid and related compounds

Abstract

Syntheses of α,α-d₂-chloroacetic acid, α,α-d₂-phenylsulfoxyacetic acid, and α,α-d₂-phenylsulfonylacetic acid are described and the suitability of these acids for conductivity measurements in aqueous (H₂O) media has been investigated. The proton-deuteron exchange reaction at the methylene position of phenylsulfoxyacetic acid has been qualitatively examined and shown to be stereoselective, i.e. the two protons (or deuterons) exchange at different rates. The solvent dependence of the chemical shifts of the methylene protons in phenylsulfoxyacetic acid and some related compounds is discussed.