Sulfinylamine
Type of organosulfur compound
From Wikipedia, the free encyclopedia
Sulfinylamines (formerly N-sulfinyl amines) are organosulfur compounds with the formula RNSO where R = an organic substituent. These compounds are, formally speaking, derivatives of HN=S=O, i.e. analogues of sulfur dioxide and of sulfur diimide. A common example is N-sulfinylaniline. The S-N bond in sulfinylamines is a dienophile.[1] They undergo [2+2] cycloaddition to ketenes.[2]
According to X-ray crystallography, sulfinylamines have planar C-N=S=O cores with syn geometry.[3]
Preparation
Sulfinylamines can be made when thionyl chloride SOCl2 reacts with a primary amine.[4] Indeed, the parent, thionylimide (HNSO), can be made that way at low temperature[5] or in the gas phase. Under standard conditions it polymerizes.[6] The corresponding trimethylsilyl compound, Me3SiNSO, is a stable liquid, albeit air-sensitive, and a common "−NSO" synthon.[7]
Reactions
A frustrated Lewis pair, such as tris(tert-butyl) phosphine and tris(pentafluorophenyl)borane, can attach to the NSO chain to yield a R'3P=N+(R)SOB−R"3 compound.[4]
Compounds
| Formula | Name | CAS No | PubChem CID | Chemspider ID | MW (g/mol) | Reference |
|---|---|---|---|---|---|---|
| HNSO | Thionylimide Sulfinylamine Sulfoximine |
13817-04-4 | 139610 | 123125 | 63.074 | [8] |
| C6H5NSO | N-Sulfinylaniline N-Thionylaniline |
1122-83-4 | 70739 | 63904 | 139.172 | [9] |
| N-Sulfinyl-2,6-diethyl benzenamine | [9] | |||||
| N-Sulfinyl-2-aminopyrimidine | 110526-12-0 | 14790782 | 141.148 | |||
| N-Sulfinyl-n-butylamine | [10] | |||||
| N-Sulfinyl-n-pentylamine | [10] |