78132-53-3Relevant articles and documents
Mechanistic Investigations into the Photochemical Oxidation of Thioketones
Ramnath, N.,Ramesh, V.,Ramamurthy, V.
, p. 112 - 114 (1981)
Singlet-oxygen reaction with dialkyl, aryl alkyl, and diaryl thioketones is found to give the corresponding sulphines and ketones in proportions depending on the nature of the thioketone.
Structure elucidation of 6-t-butyl-6-phenylpentathiane monoxides by X-ray crystallography and DFT calculations
Ishii, Akihiko,Oshida, Hideaki,Nakayama, Juzo
, p. 319 - 328 (2007/10/03)
6-t-Butyl-6-phenylpentathiane was oxidized with trifluoroperacetic acid (CF3CO3H) or dimethyldioxirane (DMD) at -20°C. Oxidation with CF3CO3H yielded pentathiane 3-oxide as the main product, whereas that of DMD gave 1- and 3-oxides. The structures of 1- and 3-oxides were finally determined by X-ray crystallographic analysis. DFT calculations of the NMR chemical shifts were performed on the chair and twist forms of the pentathiane and sixteen isomers of the monoxides with the GIAO method at the B3LYP/6-31G* level. The calculated chemical shifts were verified to be in practical agreement with the experimental data of the pentathiane and the isolated 1- and 3-oxides.
MECHANISM OF OXIDATION OF α,β-UNSATURATED THIONES BY SINGLET OXYGEN
Rac, V. Pushkara,Ramamurthy, V.
, p. 2169 - 2176 (2007/10/02)
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.