Sulfinamide is a functional group in organosulfur chemistry with the structural formula RS(O)NR'2 (where R and R' are organic substituents). This functionality is composed of a sulfur-carbon (S-C) and sulfur-nitrogen (S-N) single bonds, as well as a sulfur-oxygen double bond (S=O), resulting in a tetravalent sulfur centre (in equilibrium with its trivalent zwitterionic form). 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 (RS(O)OH).
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 (Ellman's sulfinamide), p-toluenesulfinamide (Davis' sulfinamide), and 2,4,6-trimethylbenzenesulfinamide.
- RSH + HNO → RS(O)NH2
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