• Source: 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 SOCl2 reacts with a primary amine. Indeed, the parent thionylamide, HNSO, can be made that way at low temperature.




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

Kata Kunci Pencarian:

• Sulfinylamine
• Thionyl chloride
• Benzene
• Ester
• Aldehyde
• Ether
• Methyl group
• Chlorofluorocarbon
• Urea
• Carboxylic acid