General structure of sulfinamides, showing both resonance forms
In organosulfur chemistry, sulfinamide is a functional group with the structure R−S(=O)−NR2 (where R = alkyl or aryl).[1] 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 resonance with its zwitterionic form). As a non-bonding electron pair is also present on the sulfur, these compounds are also chiral. They are sometimes referred to as S-chiral sulfinamides. Sulfinamides are amides of sulfinic acid (R−S(O)OH).
^J. G. Tillett (1981). "Sulphinamides". In Saul Patai (ed.). Sulphinic Acids, Esters and Derivatives. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. pp. 185–215. doi:10.1002/9780470772270.ch7. ISBN 978-0-471-91918-6.
In organosulfur chemistry, sulfinamide is a functional group with the structure R−S(=O)−NR2 (where R = alkyl or aryl). This functionality is composed...
organic synthesis. The related sulfinamides (R(S=O)NHR) are amides of sulfinic acids (R(S=O)OH) (see sulfinyl). Chiral sulfinamides such as tert-butanesulfinamide...
towards nucleophiles, including thiols. The initial adduct rearranges to a sulfinamide: HNO + RSH → RS(O)NH2 In biological samples, nitroxyl can be detected...
pseudoephedrine amides into synthetically useful functional groups This specific sulfinamide chiral auxiliary was initially developed by Jonathan A. Ellman, and its...
the acid strength and stability diminish in that order. Sulfonamides, sulfinamides and sulfenamides, with formulas R−SO2NR′2, R−S(O)NR′2, and R−SNR′2, respectively...
rubber using sulfur. They are related to the oxidized compounds known as sulfinamides (RS(O)NR2) and sulfonamides (RS(O)2NR2). Sulfenamides are usually prepared...
useful intermediates for preparation of other sufinyl derivatives such as sulfinamides, sulfinates, sulfoxides, and thiosulfinates. Unlike the sulfur atom in...
, Roy, A., Seibel, W.L., Portlock, D.E. (2003), "Hydroxylamines and sulfinamide as amine components in the Petasis boronic acid–Mannich reaction: synthesis...
Aspinwall, Craig A.; Miranda, Katrina M. (November 2014). "Glutathione sulfinamide serves as a selective, endogenous biomarker for nitroxyl after exposure...
S-hydroxylaminoglutathione, which then rearranges to form glutathione sulfinamide, or in the presence of GSH, forms oxidized glutathione (GSSG) and hydroxyl...
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