153 px, ''N''-Sulfinylaniline is a common sulfinylamine. Sulfinylamines (formerly ''N''-sulfinyl amines) are

organosulfur compound Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulf ...

s 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 Sulfur dioxide ( IUPAC-recommended spelling) or sulphur dioxide (traditional Commonwealth English) is the chemical compound with the formula . It is a toxic gas responsible for the odor of burnt matches. It is released naturally by volcanic ...

and of

sulfur diimide Sulfur diimides are chemical compounds of the formula S(NR)2. Structurally, they are the diimine of sulfur dioxide. The parent member, S(NH)2, is of only theoretical interest. Other derivatives where R is an organic group are stable and useful rea ...

. A common example is ''N''-sulfinylaniline. Sulfinyl amines are dienophile.Kresze, G.; Wucherpfennig, W., "Organic synthesis with imides of sulfur dioxide", Angew. Chem. Int. Ed. Engl. 1967, volume 6, 149–167. They undergo +2cycloaddition to ketenes. According to

X-ray crystallography X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angle ...

, sulfinylamines have planar C-N=S=O cores with ''syn'' geometry.. Sulfinyl Amine Group General Structure V

Preparation

Sulfinylamines can be made when

thionyl chloride Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year bein ...

SOCl₂ reacts with a

primary amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such ...

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

References

{{DEFAULTSORT:Sulfinylaniline, N- Nitrogen compounds Sulfur(IV) compounds