Thioketone

  Thioketones are organic compounds related to conventional ketones. Instead of the formula R₂C=O, thioketones, or thiones as they are also called, have the formula R₂C=S. Unhindered thioketones are typically unstable; such compounds tend to form polymers or rings.

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Preparative methods

One approach to generating thiocarbonyl-molecules entails treating a ketone with Lawesson's reagent. Other methods use of an hydrogen chloride with hydrogen sulfide. Bis(trimethylsilyl)sulfide has also been employed.^[1]

Thiobenzophenone, the prototype

  Thiobenzophenone, (C₆H₅)₂CS, is quite stable. This deep blue compound dissolves readily in organic solvents. It photooxidizes in air to benzophenone and sulfur. Since the discovery of thiobenzophenone, a variety of related thiones have been prepared by the Tokitoh group.^[2]

Selenones

The selenium versions of the thioketones are less stable than thiones.^[2] Selenobenzophenone reversibly dimerizes. It is known to react with 1,3-dienes in a Diels-Alder reaction.^[3]

See also

Thial, for a description of thioaldehydes.

References

1. ^ W. M. McGregor, D. C. Sherrington (1993). "Some Recent Synthetic Routes to Thioketones and Thioaldehydes"". Chemical Society Reviews 22: 199 - 204. doi:10.1039/CS9932200199.
2. ^ ^{a b} Okazaki, R.; Tokitoh, N. (2000). "Heavy Ketones, the Heavier Element Congeners of a Ketone". Accounts of Chemical Research 33: 625-630. doi:10.1021/ar980073b.
3. ^ Erker, G.; Hock, R.; Krüger, C.; Werner, S.; Klärner, F.-G. and Artschwager-Perl, U. (1990). "Synthesis and Cycloadditions of Monomeric Selenobenzophenone". Angewandte Chemie International Edition in English 29: 1067-68. doi:10.1002/anie.199010671.