16722-50-2Relevant articles and documents
Development of Photoactivatable Nitroxyl (HNO) Donors Incorporating the (3-Hydroxy-2-naphthalenyl)methyl Phototrigger
Zhou, Yang,Cink, Ruth B.,Fejedelem, Zachary A.,Cather Simpson,Seed, Alexander J.,Sampson, Paul,Brasch, Nicola E.
, p. 1745 - 1755 (2018/04/17)
A new family of photoactivatable HNO donors of general structure RSO2NHO-PT [where PT represents the (3-hydroxy-2-naphthalenyl)methyl (3,2-HMN) phototrigger] has been developed, which rapidly releases HNO. Photogeneration of HNO was demonstrated using the vitamin B12 derivative aquacobalamin as a trapping agent. The amount of sulfonate RSO2– produced was essentially the same as the amount of HNO released upon photolysis, providing a convenient method to indirectly quantify HNO release. Two competing pathways were also observed; a pathway involving O–N bond cleavage leading to release of a sulfonamide, and a pathway resulting in release of the parent Nhydroxysulfonamide RSO2NHOH (for HNO donors with Me- and Ph-containing leaving groups only). Up to approximately 70 % of the HNO-generating pathway was observed with the CF3-containing leaving group, with HNO generation favored for small percentages of aqueous buffer in the acetonitrile/pH 7.00 phosphate buffer solvent mixture. Characterization of the photoproducts obtained from steady-state irradiation by NMR spectroscopy showed that the desired HNO-generating pathway was less favored for HNO donors with Me- and Ph-containing leaving groups compared to the CF3-containing leaving group, suggesting that the excellent CF3-containing leaving group promotes HNO generation.
Photochemical cleavage reactions of 8-quinolinyl sulfonates in aqueous solution
Kageyama, Yoshiyuki,Ohshima, Ryosuke,Sakurama, Kazusa,Fujiwara, Yoshihisa,Tanimoto, Yoshifumi,Yamada, Yasuyuki,Aoki, Shin
experimental part, p. 1257 - 1266 (2010/05/02)
Photochemical cleavage reactions of 8-quinolinyl benzenesulfonate derivatives and related sulfonates in aqueous solutions are reported. The 8-quinolinyl benzenesulfonates undergo photolysis upon photoirradiation at 300-330 nm to give the corresponding 8-quinolinols and benzenesulfonic acids with the production of only negligible amounts of byproducts. The effects of substituent groups of the 8-quinolinyl moiety and the benzene ring on the photolysis reactions were examined. Based on steady-state mechanistic studies using a triplet sensitizer, a triplet quencher, and electron donors, it was suggested that the photolysis proceeds mainly via the homolytic cleavage of S-O bonds in the excited triplet state.
Evidences for the generation of α-alkoxy and α-alkylthioalkyl radicals upon reduction of α-functionalized alkyl phenyl sulfones. Investigation of the reduction mechanism by electrochemistry
Amatore, C.,Bayachou, M.,Bontejengout, F.,Verpeaux, J. N.
, p. 371 - 381 (2007/10/02)
The mechanism of single electron transfer reduction of α-halo-, α-alkoxy-, or α-alkylthioalkyl phenyl sulfones is investigated using cyclic or steady-state voltammetry.This study provides strong evidence that some of these sulfones can be used to generate free radicals at potentials at which they cannot be reduced.Further confirmation is obtained by indirect electrolysis.Finally, redox catalysis allows determination of standard potentials and cleavage rate constants for most of the sulfone radical anions.Keywords: sulfones / single electron transfer / electrochemical reduction / alkoxyalkyl radicals / alkylthioalkyl radicals
