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.

Additional recommended knowledge

Essential Laboratory Skills Guide

What is the Sensitivity of my Balance?

Weighing the right way

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.