Sulfinylamine
# Sulfinylamine

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. Sulfinyl amines are dienophile. They undergo [2+2] cycloaddition to ketenes.

According to X-ray crystallography, sulfinylamines have planar C-N=S=O cores with syn geometry.

## Preparation

Sulfinylamines can be made when thionyl chloride $SOCl_2$ reacts with a primary amine.

## Reactions

Mixtures of phosphine and borane derivatives can attach to the NSO chain to yield a $R'_3P=N^+(R)SOB^−R"_3$ compound. This can happen with tris(tert-butyl) phosphine and tris-(pentafluorophenyl)borane.

## Compounds

| formula | name | CAS No | PubChem CID | Chemspider ID | MW |
| - | - | - | - | - | - |
| HNSO | Thionylimide Sulfinylamine Sulfoximine | 13817-04-4 | 139610 | 123125 | 63.074 |
| $C_6H_5NSO$ | N-Sulfinylaniline N-Thionylaniline | 1122-83-4 | 70739 | 63904 | 139.172 |
| | N-sulfinyl-2,6-diethyl benzenamine | | | | |
| | N-sulfinyl-2-aminopyrimidine | 110526-12-0 | 14790782 | | 141.148 |
| | N-sulfinyl-n-butylamine | | | | |
| | N-sulfinyl-n-pentylamine | | | | |
