Sulfinylamine Explained
thumb|right|153 px|N-Sulfinylaniline is a common sulfinylamineSulfinylamines (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.[1] They undergo [2+2] cycloaddition to ketenes.[2]
According to X-ray crystallography, sulfinylamines have planar C-N=S=O cores with syn geometry.[3]
Preparation
Sulfinylamines can be made when thionyl chloride SOCl2 reacts with a primary amine.[4] Indeed, the parent thionylamide, HNSO, can be made that way at low temperature.[5]
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.[4]
Compounds
| Formula | Name | CAS No | PubChem CID | Chemspider ID | MW (g/mol) | Reference |
|---|
| HNSO | Thionylimide
Sulfinylamine
Sulfoximine | 13817-04-4 | 139610 | 123125 | 63.074 | [6] |
| C6H5NSO | N-Sulfinylaniline
N-Thionylaniline | 1122-83-4 | 70739 | 63904 | 139.172 | [7] |
| N-Sulfinyl-2,6-diethyl benzenamine | | | | | |
| N-Sulfinyl-2-aminopyrimidine | 110526-12-0 | 14790782 | | 141.148 | |
| N-Sulfinyl-n-butylamine | | | | | [8] |
| N-Sulfinyl-n-pentylamine | | | | | | |
Notes and References
- 10.1002/anie.196701491. New Methods of Preparative Organic Chemistry V: Organic Syntheses with Imides of Sulfur Dioxide. 1967. Kresze. G.. Wucherpfennig. W.. Angewandte Chemie International Edition in English. 6. 2. 149–167. 4962859.
- Book: 10.1016/B978-0-12-800170-7.00004-3. Ketenes as Privileged Synthons in the Syntheses of Heterocyclic Compounds. Part 1. Advances in Heterocyclic Chemistry. 2014. Heravi. Majid M.. Majid Momhed-Heravi. Talaei. Bahareh. 113. 143–244. 9780128001707.
- 10.1016/S0022-2860(99)00453-6. N-Sulfinylimine compounds, R–N=S=O: A chemistry family with strong temperament. 2000. Romano. R.M.. Della Védova. C.O.. Journal of Molecular Structure. 522. 1–3. 1–26. 2000JMoSt.522....1R. .
- Longobardi. Lauren E.. Wolter. Vanessa. Stephan. Douglas W.. Frustrated Lewis Pair Activation of an N-Sulfinylamine: A Source of Sulfur Monoxide. Angewandte Chemie International Edition. 12 January 2015. 54. 3. 809–812. 10.1002/anie.201409969. 25376102.
- Book: Roesky, H. W.. Sulfur in Organic and Inorganic Chemistry. 1. Alexander. Senning. 1971. Marcel Dekker. New York. 70-154612. 0-8247-1615-9. The Sulfur - Nitrogen Bond. 24.
- Kresze. G.. Maschke. A.. Albrecht. R.. Bederke. K.. Patzschke. H. P.. Smalla. H.. Trede. A.. Organic N-Sulfinyl Compounds. Angewandte Chemie International Edition in English. February 1962. 1. 2. 89–98. 10.1002/anie.196200891.
- Romano. R.M. Della Védova. C.O. Boese. R. 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. January 1999. 475. 1. 1–4. 10.1016/S0022-2860(98)00439-6. 1999JMoSt.475....1R .
- Ammoscato. Vince. Part I. A study of the alkylation chemistry of N-sulfinyl amines. Part II. Attempted preparation of the camphor imine of stereospecifically deuterated glycine.. Electronic Theses and Dissertations . University of Windsor. 28 January 2018. en. 1990.
