From Wikipedia, the free encyclopedia
  (Redirected from Thione)
Jump to: navigation, search
"Thione" redirects here. For the beetle, see Thione (genus).
Thioketones general formulae

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, which is reflected by the prefix "thio-" in the name of the functional group. Unhindered alkylthioketones typically tend to form polymers or rings.[1]

Preparative methods[edit]

Thiones are usually prepared from ketones using reagents that exchange S and O atoms. A common reagent is phosphorus pentasulfide[2] and its derivative Lawesson's reagent. Other methods uses a mixture of hydrogen chloride combined with hydrogen sulfide. Bis(trimethylsilyl)sulfide has also been employed.[3]

Thiobenzophenone and selenobenzophenone, the prototypes[edit]

Skeletal formula of thiobenzophenone

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] Selenketones, the selenium versions of the thioketones, are more reactive 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[edit]


  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. 
  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. 
  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. 
  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. 

External links[edit]