Thioketone
From Wikipedia, the free encyclopedia
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.
Contents |
[edit] 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]
[edit] 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]
[edit] 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]
[edit] See also
Thial, for a description of thioaldehydes.
[edit] References
- ^ W. M. McGregor, D. C. Sherrington (1993). "Some Recent Synthetic Routes to Thioketones and Thioaldehydes"". Chemical Society Reviews 22: 199–204. doi:.
- ^ a b Okazaki, R.; Tokitoh, N. (2000). "Heavy Ketones, the Heavier Element Congeners of a Ketone". Accounts of Chemical Research 33: 625–630. doi:.
- ^ 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:.
