25862-08-2Relevant academic research and scientific papers
Discovery, characterisation, and utilisation of selenoxide-sulfonic acid salts: A new class of selenoxide-based oxidant and stable selenoxide equivalent
Procter, D. John,Thornton-Pett, Mark,Rayner, Christopher M.
, p. 1841 - 1854 (2007/10/03)
The preparation and characterisation of a novel class of salts of selenoxides with sulfonic acids are described. They are readily prepared by simple addition of the sulfonic acid to a solution of selenoxide, and removal of solvent. In most cases they are colourless crystalline solids and are considerably more stable than the parent selenoxides, allowing full characterisation and X-ray crystallographic analysis. They also efficiently oxidise sulfides to sulfoxides, with no overoxidation, and clean regeneration of selenide. Their structure has been confirmed by 1H NMR spectroscopy and X-ray crystallography.
Preparation of selenoxides from the catalytic autoxidation of organoselenides with nitrogen oxides
Bosch, Eric,Kochi, Jay K.
, p. 2731 - 2738 (2007/10/03)
Various alkyl, aryl and benzyl selenides (RSeR') are readily coverted in high yields to the corresponding selenoxide in the presence of dioxygen and catalytic amounts of either nitrogen dioxide, nitrosonium cation or nitric oxide in acetic acid.The selenoxides are initially isolated as the acetic acid adducts (from which the free selenoxides are readily liberated by treatment with base).Nitrogen dioxide is also capable of the stoichiometric oxidation of the selenoethers; and the electron donor-acceptor or EDA complex with nitrosonium, i.e. NO3(1-) is formed as the first intermediate by the selenoether-induced disproportionation of NO2.The critical role of the nitrosonium EDA complex is further demonstrated by the production of selenoxide by an alternative (low-temperature) photochemical procedure involving the deliberate irradiation of the charge-transfer absorption band of NO3(1-).A scheme is shown that presents the sequence of redox changes of the nitrogen oxides involved in the catalytic conversion of selenoethers to their selenoxides.
