{{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 with 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 considers the term 'sulfine' obsolete,<ref>{{GoldBookRef|title=sulfines| file = S06108}}</ref> preferring instead thiocarbonyl ''S''-oxide; 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 synthesis, in which a sulfinyl halide reacts with a hindered base. For example, syn-propanethial-S-oxide, responsible for eye-watering effects of cutting onions, is produced so from 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 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°.
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==See also== * Sulfene - related functional group with the formula H<sub>2</sub>C=SO<sub>2</sub> *Ethenone *Heterocumulene
==References== {{reflist}}
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Category:Organosulfur compounds Category:Heteroallenes