Thioketone

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.

Preparative methods

One approach to generating thiocarbonyl-molecules entails treating a ketone with Lawesson's reagent. Other methods uses a mixture of hydrogen chloride with hydrogen sulfide. Bis(trimethylsilyl)sulfide has also been employed. [cite journal| title = Some Recent Synthetic Routes to Thioketones and Thioaldehydes"| author =W. M. McGregor, D. C. Sherrington| journal = Chemical Society Reviews | volume = 22| pages = 199–204| year = 1993| doi = 10.1039/CS9932200199]

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.cite journal | author = Okazaki, R.; Tokitoh, N. | title = Heavy Ketones, the Heavier Element Congeners of a Ketone | journal = Accounts of Chemical Research | year = 2000 | volume = 33 | pages = 625–630 | doi = 10.1021/ar980073b]

elenones

The selenium versions of the thioketones are less stable than thiones. Selenobenzophenone reversibly dimerizes. It is known to react with 1,3-dienes in a Diels-Alder reaction. [cite journal | author = Erker, G.; Hock, R.; Krüger, C.; Werner, S.; Klärner, F.-G. and Artschwager-Perl, U. | title = Synthesis and Cycloadditions of Monomeric Selenobenzophenone | journal = Angewandte Chemie International Edition in English | year = 1990 | volume = 29 | pages = 1067–68 | doi = 10.1002/anie.199010671]

ee also

Thial, for a description of thioaldehydes.

References

External links

* [http://goldbook.iupac.org/T06356.html Definition of Thioketones in the IUPAC Golden Book]


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