General structure of anN-sulfinyl amineN-Sulfinylaniline is a common sulfinylamine
Sulfinylamines (formerlyN-sulfinyl amines) areorganosulfur compounds with the formula RNSO where R = an organic substituent. These compounds are, formally speaking, derivatives of HN=S=O, i.e. analogues ofsulfur dioxide and ofsulfur diimide. A common example isN-sulfinylaniline. Sulfinyl amines aredienophile.[1] They undergo [2+2] cycloaddition to ketenes.[2]
According toX-ray crystallography, sulfinylamines have planar C-N=S=O cores withsyn geometry.[3]
Sulfinylamines can be made whenthionyl chloride SOCl2 reacts with aprimary amine.[4] Indeed, the parent thionylamide, HNSO, can be made that way at low temperature.[5]
Afrustrated 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]
^Kresze, G.; Wucherpfennig, W. (1967). "New Methods of Preparative Organic Chemistry V: Organic Syntheses with Imides of Sulfur Dioxide".Angewandte Chemie International Edition in English.6 (2):149–167.doi:10.1002/anie.196701491.PMID4962859.
^abLongobardi, Lauren E.; Wolter, Vanessa; Stephan, Douglas W. (12 January 2015). "Frustrated Lewis Pair Activation of anN-Sulfinylamine: A Source of Sulfur Monoxide".Angewandte Chemie International Edition.54 (3):809–812.doi:10.1002/anie.201409969.PMID25376102.
^Roesky, H. W. (1971). "The Sulfur–Nitrogen Bond". In Senning, Alexander (ed.).Sulfur in Organic and Inorganic Chemistry. Vol. 1. New York: Marcel Dekker. p. 24.ISBN0-8247-1615-9.LCCN70-154612.
^Kresze, G.; Maschke, A.; Albrecht, R.; Bederke, K.; Patzschke, H. P.; Smalla, H.; Trede, A. (February 1962). "Organic N-Sulfinyl Compounds".Angewandte Chemie International Edition in English.1 (2):89–98.doi:10.1002/anie.196200891.
^abRomano, R.M; Della Védova, C.O; Boese, R (January 1999). "A solid state study of the configuration and conformation of OSN–R (R=C6H5 and C6H3(CH3–CH2)2-2,6)".Journal of Molecular Structure.475 (1):1–4.Bibcode:1999JMoSt.475....1R.doi:10.1016/S0022-2860(98)00439-6.
