Rao, V Pushkara and Ramamurthy, V (1985) Mechanism of oxidation of Î±,Î²-unsaturated thiones by singlet oxygen. In: Tetrahedron, 41 (11). pp. 2169-2176.
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Photo-oxidation of Î±,Î²-unsaturated thiones yields the corresponding ketones as the only product. Studies carried out on three systems, namely thioketones, Î±,Î²-unsaturated thiones and thioketenes, have revealed that there exists a similarity in their mechanism of oxidation. It has been suggested that the thiocarbonyl chromophore is the site of attack by singlet oxygen in Î±,Î²-unsaturated thiones and that the adjacent C-C double bond is inert under these conditions. Absence of sulphine during the oxidation of Î±,Î²-unsaturated thiones is attributed to the electronic factors operating on the zwitterionic/diradical intermediate. While Î±,Î²-unsaturated ketones are poorly reactive, Î±,Î²-unsaturated thiones are highly reactive toward singlet oxygen.
|Item Type:||Journal Article|
|Additional Information:||The copyright of this article belongs to Elsevier Science.|
|Department/Centre:||Division of Chemical Sciences > Organic Chemistry|
|Date Deposited:||24 Nov 2009 10:09|
|Last Modified:||19 Sep 2010 05:35|
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