Sulfinylamine: Difference between revisions
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{{short description|Type of organosulfur compound}} |
{{short description|Type of organosulfur compound}} |
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[[file:PhNSO-2.svg|thumb|right|153 px|[[N-Sulfinylaniline|''N''-Sulfinylaniline]] is a common sulfinylamine.]] |
[[file:PhNSO-2.svg|thumb|right|153 px|[[N-Sulfinylaniline|''N''-Sulfinylaniline]] is a common sulfinylamine.]] |
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'''Sulfinylamines''' are [[organosulfur compound]]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]] and of [[sulfur diimide]]. A common example is ''N''-sulfinylaniline. Sulfinyl amines are [[dienophile]].<ref name= Kresze>Kresze, G.; Wucherpfennig, W., "Organic synthesis with imides of sulfur dioxide", Angew. Chem. Int. Ed. Engl. 1967, volume 6, 149-167. {{DOI|10.1002/anie.196701491}}</ref> They undergo [2+2] cycloaddition to ketenes.<ref>{{cite book |doi=10.1016/B978-0-12-800170-7.00004-3|title=Ketenes as Privileged Synthons in the Syntheses of Heterocyclic Compounds. Part 1|series=Advances in Heterocyclic Chemistry|year=2014|last1=Heravi|first1=Majid M.|last2=Talaei|first2=Bahareh|volume=113|pages=143–244|isbn=9780128001707}}</ref> |
'''Sulfinylamines''' (formerly '''N-sulfinyl amines''') are [[organosulfur compound]]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]] and of [[sulfur diimide]]. A common example is ''N''-sulfinylaniline. Sulfinyl amines are [[dienophile]].<ref name= Kresze>Kresze, G.; Wucherpfennig, W., "Organic synthesis with imides of sulfur dioxide", Angew. Chem. Int. Ed. Engl. 1967, volume 6, 149-167. {{DOI|10.1002/anie.196701491}}</ref> They undergo [2+2] cycloaddition to ketenes.<ref>{{cite book |doi=10.1016/B978-0-12-800170-7.00004-3|title=Ketenes as Privileged Synthons in the Syntheses of Heterocyclic Compounds. Part 1|series=Advances in Heterocyclic Chemistry|year=2014|last1=Heravi|first1=Majid M.|last2=Talaei|first2=Bahareh|volume=113|pages=143–244|isbn=9780128001707}}</ref> |
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According to [[X-ray crystallography]], sulfinylamines have planar C-N=S=O cores with ''syn'' geometry.<ref>{{cite journal|doi=10.1016/S0022-2860(99)00453-6|title=N-Sulfinylimine compounds, R–N=S=O: A chemistry family with strong temperament|year=2000|last1=Romano|first1=R.M.|last2=Della Védova|first2=C.O.|journal=Journal of Molecular Structure|volume=522|issue=1–3|pages=1–26|bibcode=2000JMoSt.522....1R}}.</ref> |
According to [[X-ray crystallography]], sulfinylamines have planar C-N=S=O cores with ''syn'' geometry.<ref>{{cite journal|doi=10.1016/S0022-2860(99)00453-6|title=N-Sulfinylimine compounds, R–N=S=O: A chemistry family with strong temperament|year=2000|last1=Romano|first1=R.M.|last2=Della Védova|first2=C.O.|journal=Journal of Molecular Structure|volume=522|issue=1–3|pages=1–26|bibcode=2000JMoSt.522....1R}}.</ref> |
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[[File:Sulfinyl Amine Group General Structure V.1.png|thumb|line drawing of general structure of an N-sulfinyl amine]] |
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==Preparation== |
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Sulfinylamines can be made when [[thionyl chloride]] SOCl<sub>2</sub> reacts with a [[primary amine]].<ref name="longo">{{cite journal|last1=Longobardi|first1=Lauren E.|last2=Wolter|first2=Vanessa|last3=Stephan|first3=Douglas W.|title=Frustrated Lewis Pair Activation of an ''N''-Sulfinylamine: A Source of Sulfur Monoxide|journal=Angewandte Chemie International Edition|date=12 January 2015|volume=54|issue=3|pages=809–812|doi=10.1002/anie.201409969|pmid=25376102}}</ref> |
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==Reactions== |
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Mixtures of phosphine and borane derivatives can attach to the NSO chain to yield a R'<sub>3</sub>P=N<sup>+</sup>(R)SOB<sup>−</sup>R"<sub>3</sub> compound. This can happen with tris(''tert''-butyl) phosphine and tris-(pentafluorophenyl)borane.<ref name="longo"/> |
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==Compounds== |
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{|class="wikitable" |
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!formula |
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!name |
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!CAS No |
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!PubChem CID |
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!Chemspider ID |
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!MW |
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!ref |
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|HNSO |
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|[[Thionylimide]]<br/>Sulfinylamine<br/>Sulfoximine |
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|13817-04-4 |
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|139610 |
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|123125 |
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|63.074 |
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|<ref name="kres">{{cite journal|last1=Kresze|first1=G.|last2=Maschke|first2=A.|last3=Albrecht|first3=R.|last4=Bederke|first4=K.|last5=Patzschke|first5=H. P.|last6=Smalla|first6=H.|last7=Trede|first7=A.|title=Organic N-Sulfinyl Compounds|journal=Angewandte Chemie International Edition in English|date=February 1962|volume=1|issue=2|pages=89–98|doi=10.1002/anie.196200891}}</ref> |
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|C<sub>6</sub>H<sub>5</sub>NSO |
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|[[N-Sulfinylaniline|''N''-Sulfinylaniline]]<br>''N''-Thionylaniline |
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|1122-83-4 |
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|70739 |
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|63904 |
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|139.172 |
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|<ref name="benzamine">{{cite journal|last1=Romano|first1=R.M|last2=Della Védova|first2=C.O|last3=Boese|first3=R|title=A solid state study of the configuration and conformation of OSN–R (R=C6H5 and C6H3(CH3–CH2)2-2,6)|journal=Journal of Molecular Structure|date=January 1999|volume=475|issue=1|pages=1–4|doi=10.1016/S0022-2860(98)00439-6}}</ref> |
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|''N''-sulfinyl-2,6-diethyl benzenamine |
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|<ref name="benzamine"/> |
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|N-sulfinyl-2-aminopyrimidine |
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|110526-12-0 |
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|14790782 |
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|141.148 |
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|N-sulfinyl-n-butylamine |
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|<ref name="ammo">{{cite web|last1=Ammoscato|first1=Vince|title=Part I. A study of the alkylation chemistry of N-sulfinyl amines. Part II. Attempted preparation of the camphor imine of stereospecifically deuterated glycine.|url=https://scholar.uwindsor.ca/etd/3002/|publisher=University of Windsor|accessdate=28 January 2018|language=en|date=1990}}</ref> |
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|N-sulfinyl-n-pentylamine |
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|<ref name="ammo"/> |
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==References== |
==References== |
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<references />{{Organic-compound-stub}} |
{{Reflist}} |
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<references /> |
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{{Organic-compound-stub}} |
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{{DEFAULTSORT:Sulfinylaniline, N-}} |
{{DEFAULTSORT:Sulfinylaniline, N-}} |
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[[Category:Nitrogen compounds]] |
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[[Category:Sulfur(IV) compounds]] |
[[Category:Sulfur(IV) compounds]] |
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Revision as of 15:59, 3 July 2021
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.[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]
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 | ref |
|---|---|---|---|---|---|---|
| HNSO | Thionylimide Sulfinylamine Sulfoximine |
13817-04-4 | 139610 | 123125 | 63.074 | [5] |
| C6H5NSO | N-Sulfinylaniline N-Thionylaniline |
1122-83-4 | 70739 | 63904 | 139.172 | [6] |
| N-sulfinyl-2,6-diethyl benzenamine | [6] | |||||
| N-sulfinyl-2-aminopyrimidine | 110526-12-0 | 14790782 | 141.148 | |||
| N-sulfinyl-n-butylamine | [7] | |||||
| N-sulfinyl-n-pentylamine | [7] |
References
- ^ Kresze, G.; Wucherpfennig, W., "Organic synthesis with imides of sulfur dioxide", Angew. Chem. Int. Ed. Engl. 1967, volume 6, 149-167. doi:10.1002/anie.196701491
- ^ Heravi, Majid M.; Talaei, Bahareh (2014). Ketenes as Privileged Synthons in the Syntheses of Heterocyclic Compounds. Part 1. Advances in Heterocyclic Chemistry. Vol. 113. pp. 143–244. doi:10.1016/B978-0-12-800170-7.00004-3. ISBN 9780128001707.
- ^ Romano, R.M.; Della Védova, C.O. (2000). "N-Sulfinylimine compounds, R–N=S=O: A chemistry family with strong temperament". Journal of Molecular Structure. 522 (1–3): 1–26. Bibcode:2000JMoSt.522....1R. doi:10.1016/S0022-2860(99)00453-6..
- ^ a b Longobardi, Lauren E.; Wolter, Vanessa; Stephan, Douglas W. (12 January 2015). "Frustrated Lewis Pair Activation of an N-Sulfinylamine: A Source of Sulfur Monoxide". Angewandte Chemie International Edition. 54 (3): 809–812. doi:10.1002/anie.201409969. PMID 25376102.
- ^ 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.
- ^ a b Romano, 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. doi:10.1016/S0022-2860(98)00439-6.
- ^ a b Ammoscato, Vince (1990). "Part I. A study of the alkylation chemistry of N-sulfinyl amines. Part II. Attempted preparation of the camphor imine of stereospecifically deuterated glycine". University of Windsor. Retrieved 28 January 2018.
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