Sulfinamide

In organosulfur chemistry, sulfinamide is a functional group with the structure R−S(O)−NR2 (where R = alkyl or aryl).

[2] 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.

Sulfinamides are traditionally produced by the reaction of sulfinyl chlorides with primary or secondary amines.

[1] They also arise by the addition of Grignard reagents to sulfinylamines, followed by protonation: Yet another route entails peracid-oxidation of sulfenylphthalimides, which gives sulfinylphthalimides.

[4][5][6] Sulfinamides arise in nature by the addition of nitroxyl (HNO) to thiols:[7]

General structure of sulfinamides, showing both correct zwitterionic and "expanded octet" simplified convention
Structure of Davis' sulfinamide ( p -tolylsulfinamide), highlighting the pyramidal nature of the S center [ 3 ]