Thioketene

The general structure of thioketenes

Thioketenes are organosulfur compounds analogous to ketenes with the general formula R₂C=C=S, where R is alkyl or aryl. Thioketene (ethenthione) is also the name of the compound CH₂=C=S, which is the simplest thioketene. Thioketenes are reactive, tending to polymerize. Some thioketenes are produced as transient species upon pyrolysis of 1,2,3-thiadiazoles.^[1]

Bis(trifluoromethyl)thioketene ((CF₃)₂C=C=S) is a rare example of a stable thioketene.^[2] Another stable thioketene is carbon subsulfide (S=C=C=C=S).

It has been suggested that thioketene could be involved in cell damage processes.^[3]

References[]

^ Otto-Albrecht Neuman (Editor). Rompps Encyclopedia of Chemistry, Frank'sche Publishing House, Stuttgart, 1983, 8. Edition, p. 4242, ISBN 3-440-04513-7.
^ Raasch, Maynard S. (1970). "Bis(trifluoromethyl)thioketene. I. Synthesis and cycloaddition reactions". J. Org. Chem. 35 (10): 3470–3483. doi:10.1021/jo00835a064.
^ Dekant, Wolfgang; Urban, Gudrun; Goersmann, Claus; Anders, M.W. (1991). "Thioketene formation from α-haloalkenyl 2-nitrophenyl disulfides: models for biological reactive intermediates of cytotoxic S-conjugates". J. Am. Chem. Soc. 113 (13): 5120–5122. doi:10.1021/ja00013a090.

[1] Otto-Albrecht Neuman (Editor). Rompps Encyclopedia of Chemistry, Frank'sche Publishing House, Stuttgart, 1983, 8. Edition, p. 4242, ISBN 3-440-04513-7.

[2] Raasch, Maynard S. (1970). "Bis(trifluoromethyl)thioketene. I. Synthesis and cycloaddition reactions". J. Org. Chem. 35 (10): 3470–3483. doi:10.1021/jo00835a064.

[3] Dekant, Wolfgang; Urban, Gudrun; Goersmann, Claus; Anders, M.W. (1991). "Thioketene formation from α-haloalkenyl 2-nitrophenyl disulfides: models for biological reactive intermediates of cytotoxic S-conjugates". J. Am. Chem. Soc. 113 (13): 5120–5122. doi:10.1021/ja00013a090.

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