Chemical shift nonequivalence of sulfinates: Structural,solvent and temperature effects

The structural, solvent and temperature effects on the PMR spectra of several alkyl alkanesulfinates and arenesulfinates are discussed. A low order intrinsic nonequivalence was observed in substituents alpha to the sulfinate sulfur atom, the nonequivalence being significantly less than in sulfoxides, and solvent and temperature dependent. Nonequivalence of diastereotopic substituents on the ester oxygen exceeded nonequivalence in similar sulfoxides and is largely insensitive to temperatures from 25° to 120°C. Benzene complexes with sulfinates greatly enhancing the proton nonequivalence of alpha substituents apparently by causing a further shielding of the already more shielded nonequivalent protons.