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In organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...
, thioketenes are organosulfur compounds analogous to ketene
In organic chemistry, a ketene is an organic compound of the form , where R and R' are two arbitrary monovalent chemical groups (or two separate substitution sites in the same molecule). The name may also refer to the specific compound ethen ...
s with the general formula , where R is alkyl
In organic chemistry, an alkyl group is an alkane missing one hydrogen.
The term ''alkyl'' is intentionally unspecific to include many possible substitutions.
An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...
or aryl
In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as ...
. Thioketene (ethenthione) is also the name of the compound , which is the simplest thioketene. Thioketenes are reactive, tending to polymerize. Some thioketenes are produced as transient species upon pyrolysis
The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''py ...
of 1,2,3-thiadiazoles.
Bis(trifluoromethyl)thioketene () is a rare example of a stable thioketene. Another stable thioketene is carbon subsulfide
Carbon subsulfide is an organic, sulfur-containing chemical compound with the formula and structure . This deep red liquid is immiscible with water but soluble in organic solvents. It readily polymerizes at room temperature to form a hard ...
().
It has been suggested that thioketene could be involved in cell damage processes.{{cite journal , last1 = Dekant , first1 = Wolfgang , last2 = Urban , first2 = Gudrun , last3 = Goersmann , first3 =Claus, last4 = Anders , first4 = M.W. , year = 1991 , title = Thioketene formation from α-haloalkenyl 2-nitrophenyl disulfides: models for biological reactive intermediates of cytotoxic S-conjugates , journal = J. Am. Chem. Soc. , volume = 113 , issue = 13, pages = 5120–5122 , doi = 10.1021/ja00013a090
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