# Sulfine

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{{Chembox
| ImageFile = Sulfinylmethane.svg
| ImageSize = 120px
| PIN = Methylidene-λ<sup>4</sup>-sulfanone
| OtherNames = sulfine
| Section1 = {{Chembox Identifiers
| CASNo = 40100-16-1
| PubChem = 142407
| ChemSpiderID = 125626
| SMILES = C=S=O
| StdInChI= 1S/CH2OS/c1-3-2/h1H2
| StdInChIKey = IWOKCMBOJXYDEE-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=1|H=2|O=1|S=1
}}
}}

'''Sulfinylmethane''' or '''sulfine''' is an [organic compound](/source/organic_compound) with [molecular formula](/source/molecular_formula) H<sub>2</sub>CSO. It is the simplest sulfine. Sulfines are chemical compounds with the general structure XY=SO.<ref name=eros>{{cite journal|surname1=Binne Zwanenburg|title=Sulfine Chemistry|journal=Phosphorus, Sulfur, and Silicon and the Related Elements|volume=43|year=1989|issue=1–2|pages=1–24|doi=10.1080/10426508908040276}}</ref> [IUPAC](/source/IUPAC) considers the term 'sulfine' obsolete,<ref>{{GoldBookRef|title=sulfines| file = S06108}}</ref> preferring instead [thiocarbonyl ''S''-oxide](/source/Organosulfur_compounds); despite this, the use of the term sulfine still predominates in the chemical literature.

==Substituted sulfines==
The parent sulfine H<sub>2</sub>CSO is very labile, whereas substituted derivatives are more conveniently isolated.  

One route is a variant of [ketene](/source/ketene) synthesis, in which a [sulfinyl halide](/source/sulfinyl_halide) reacts with a [hindered base](/source/hindered_base).   For example, [syn-propanethial-S-oxide](/source/syn-propanethial-S-oxide), responsible for eye-watering effects of cutting onions, is produced so from [allicin](/source/allicin).<ref>{{cite journal |author1=Block E., Gillies J.Z., Gillies C.W., Bazzi A.A., Putman D., Revelle L.K., Wang D., Zhang X. |title=''Allium'' Chemistry: Microwave Spectroscopic Identification, Mechanism of Formation, Synthesis, and Reactions of (''E'',''Z'')-Propanethial ''S''-Oxide, the Lachrymatory Factor of the Onion (''Allium cepa'')|journal=J. Am. Chem. Soc.|volume=118|pages=7492–7501|doi=10.1021/ja960722j |year=1996 |issue=32 |bibcode=1996JAChS.118.7492B }}</ref> 

Another route is oxidation, as with [thiobenzophenone](/source/thiobenzophenone) from diphenylsulfine:<ref>{{cite journal|journal=Acta Crystallogr.|year=1979|volume=B35|pages=1179–1182|doi=10.1107/S0567740879005835|title=The crystal and molecular structures of the thiobenzophenone S-oxide and thiobenzophenone|author=G. Rindorf |author2=L. Carlsen |issue=5|bibcode=1979AcCrB..35.1179R }}</ref>
:(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>C=S  +  [O]  →   (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>C=S=O
thumb|left|220 px|Structure of diphenylsulfine. Selected distances and angles: r<sub>S=O</sub> = 1.468, r<sub>C=S</sub> = 1.612 Å, <<sub>C=S=O</sub> = 113.7°.

{{clear}}

==See also==
* [Sulfene](/source/Sulfene) - related functional group with the formula H<sub>2</sub>C=SO<sub>2</sub>
*[Ethenone](/source/Ethenone)
*[Heterocumulene](/source/Heterocumulene)

==References==
{{reflist}}

{{Authority control}}

Category:Organosulfur compounds
Category:Heteroallenes

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Adapted from the Wikipedia article [Sulfine](https://en.wikipedia.org/wiki/Sulfine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Sulfine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.