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Sulfinamide

In organosulfur chemistry, sulfinamide is a functional group with the structure R−S(O)−NR2. This functionality is composed of a sulfur-carbon single bond, a sulfur-nitrogen single bond, and a sulfur-oxygen (S-O) bond. As a non-bonding electron pair is present on the sulfur, the sulfur atom is a stable stereogenic centre, and so these compounds are chiral. They are sometimes referred to as S-chiral sulfinamides. Sulfinamides are amides of sulfinic acid.

Structure
Sulfinamides do not undergo inversion. They can therefore be synthesised and/or isolated in enantiopure forms. This has led to their use as chiral ammonia equivalents. Chiral sulfinamides such as tert-butanesulfinamide, p-toluenesulfinamide and 2,4,6-trimethylbenzenesulfinamide are all chiral auxiliaries. ==Synthesis==
Synthesis
Sulfinamides are traditionally produced by the reaction of sulfinyl chlorides with primary or secondary amines. They also arise by the addition of Grignard reagents to sulfinylamines, followed by protonation: :RMgX + R'N=S=O → RS(O)(NR'MgX) :RS(O)(NR'MgX) + H2O → RS(O)(NR'H) + "MgX(OH)" Yet another route entails peracid-oxidation of sulfenylphthalimides, which gives sulfinylphthalimides. ==Examples==
Examples
A common sulfinamide is tert-butanesulfinamide (Ellman's sulfinamide), p-toluenesulfinamide (Davis' sulfinamide), and mesitylsulfinamide. Sulfinamides arise in nature by the addition of nitroxyl (HNO) to thiols: :RSH + HNO → RS(O)NH2 ==References==
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