99649-01-1Relevant academic research and scientific papers
MECHANISM OF OXIDATION OF α,β-UNSATURATED THIONES BY SINGLET OXYGEN
Rac, V. Pushkara,Ramamurthy, V.
, p. 2169 - 2176 (1985)
Photo-oxidation of α,β-unsaturated thiones yields the corresponding ketones as the only product.Studies carried out three systems, namely thioketones, α,β-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 α,β-unsaturated thiones and that the adjacent C-C double bond is inert under these conditions.Absence of sulphine during the oxidation of α,β-unsaturated thiones is attributed to the electronic factors operating on the zwitterionic / diradical intermediate.While α,β-unsaturated ketones are poorly reactive, α,β-unsaturated thiones are highly reactive toward singlet oxygen.
