Sulfinylamine


Sulfinylamines 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 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 SOCl2 reacts with a primary amine. Indeed, the parent thionylimide, HNSO, can be made that way at low temperature.

Reactions

A frustrated [Lewis pair], such as tris phosphine and trisborane, can attach to the NSO chain to yield a R'3P=N+SOB−R"3 compound.