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Organic compounds with the structure >C=C=S From Wikipedia, the free encyclopedia
In organic chemistry, thioketenes are organosulfur compounds analogous to ketenes with the general formula R2C=C=S, where R is alkyl or aryl. The parent thioketene (ethenthione) has the formula CH2=C=S. It is the simplest thioketene.[1] Thioketene is stable as a gas, but like most thioketenes, it polymerizes upon condensation.
Some thioketenes are produced as transient species upon pyrolysis of 1,2,3-thiadiazoles.[2] It has been suggested that thioketene could be involved in cell damage processes.[3]
Thioketenes can be stabilized by either steric protection or by electronic effects. Thus, di-tert-butylthioketene is easily isolated and air-stable.[4] Several examples have been characterized by X-ray crystallography. The C=S distance is 157 pm and the C=C distance is 124 pm, both bonds being suitable for the C=C=S assignment. The violet color characteristic of thioketenes indicates the small HOMO-LUMO gap.[5] These compound are prepared by treatment of the acid chloride with phosphorus pentasulfide as described by the following idealized equation:
Bis(trifluoromethyl)thioketene ((CF3)2C=C=S) is an example of an electronically stabilized thioketene.[6]
Thioketenes are electrophilic. They add amines to give thioamides:[4]
With peroxyacids, they produce thioketene-S-oxides:[5]
Thioketenes bind to metal carbonyls giving adducts.[7]
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