Thioketone

Thioketones (also known as thiones or thiocarbonyls) are organosulfur compounds related to conventional ketones. Instead of the formula R2C=O, thioketones have the formula R2C=S. Unhindered alkylthioketones are typically unstable; such compounds tend to form polymers or rings.[1]

Contents

Preparative methods

Thiones are usually prepared from ketones. A common reagent is phosphorus pentasulfide.[2] Lawesson's reagent, a derivative of P4S10, can also be used. Other methods uses a mixture of hydrogen chloride with hydrogen sulfide. Bis(trimethylsilyl)sulfide has also been employed.[3]

Thiobenzophenone, the prototype

Thiobenzophenone, (C6H5)2CS, is a stable deep blue compound that dissolves readily in organic solvents. It photooxidizes in air to benzophenone and sulfur. Since its discovery, a variety of related thiones have been prepared.[4]

Selones

The selenium versions of the thioketones are less stable than thiones.[4] Selenobenzophenone reversibly dimerizes. It is known to undergo cycloaddition with 1,3-dienes in a reaction similar to the Diels-Alder reaction.[5]

See also

References

  1. ^ Kroto, H.; Landsberg, B. M.; Suffolk, R. J.; Vodden, A. (1974). "The photoelectron and microwave spectra of the unstable species thioacetaldehyde, CH3CHS, and thioacetone, (CH3)2CS". Chemical Physics Letters 29 (2): 265–269. Bibcode 1974CPL....29..265K. doi:10.1016/0009-2614(74)85029-3.  edit
  2. ^ Vivek Polshettiwar, M.P. Kaushik "A new, efficient and simple method for the thionation of ketones to thioketones using P4S10/Al2O3" Tetrahedron Letters 2004, Volume 45, 6255-6257. doi:10.1016/j.tetlet.2004.06.091
  3. ^ Mcgregor, W. M.; Sherrington, D. C. (1993). "Some recent synthetic routes to thioketones and thioaldehydes". Chemical Society Reviews 22 (3): 199. doi:10.1039/CS9932200199.  edit
  4. ^ a b Okazaki, R.; Tokitoh, N. (2000). "Heavy ketones, the heavier element congeners of a ketone". Accounts of chemical research 33 (9): 625–630. doi:10.1021/ar980073b. PMID 10995200.  edit
  5. ^ Erker, G.; Hock, R.; Krüger, C.; Werner, S.; Klärner, F. G.; Artschwager-Perl, U. (1990). "Synthesis and Cycloadditions of Monomeric Selenobenzophenone". Angewandte Chemie International Edition in English 29 (9): 1067. doi:10.1002/anie.199010671.  edit

External links