Sulfinamide
Sulfinamide is a functional group in organosulfur chemistry with the structural formula RSNR'2. This functionality is composed of a sulfur-carbon and sulfur-nitrogen single bonds, as well as a sulfur-oxygen double bond, resulting in a tetravalent sulfur centre. As a non-bonding electron pair is also present on the sulfur, these compounds are also chiral, and are referred to as S-chiral sulfinamides. Sulfinamides are amides of sulfinic acid.
As sulfinamides do not undergo inversion, their chirality remains conserved and they can therefore be synthesised and/or isolated in enantiopure forms. This has led to their use as chiral ammonia equivalents and more broadly as chiral auxiliaries. The most commonly sulfinamides for these synthetic applications are tert-butanesulfinamide, p-toluenesulfinamide, and 2,4,6-trimethylbenzenesulfinamide.
Sulfinamides arise in nature by the addition of nitroxyl to thiols:
