68385-34-2Relevant academic research and scientific papers
SYNTHESIS OF STABLE OXAZOLIDINE NITROXYL RADICALS WITH METHOXY GROUPS AT THE α-CARBON ATOMS TO THE RADICAL SITE
Bakunova, S. M.,Grigor'ev, I. A.,Kirilyuk, I. A.,Gatilov, Yu. V.,Bagryanskaya, I, Yu.,Volodarskii, L. B.
, p. 758 - 764 (2007/10/02)
The condensation of α-hydroxyaminoalcohols with aldehydes and acetone gave 3-hydroxyoxazolidines and tautomeric N-(2-hydroxyethyl)-α-arylnitrones, whose oxidation by PbO2 in methanol leads to stable oxazolidine nitroxyl radicals with methoxy groups at Cs
Electrochemical Reduction of Tertiary Nitroalkanes to Amines
Ohmori, Hidenobu,Furusako, Shoji,Kashu, Mieko,Ueda, Chihiro,Masui, Masaichiro
, p. 3345 - 3353 (2007/10/02)
Electrochemical reduction of tertiary nitroalkanes, 2-substituted-1,1-dimethyl-1-nitroethanes (1), was investigated in aqueous buffer solutions.In polarography, 1 with a phenyl group and/or a hydroxyl group at the 2-position showed an ill-defined wave in the weakly acidic and neutral pH region at relatively high negative potentials, in addition to a well-defined wave arising from the reduction of 1 to the corresponding hydroxylamine (2).Controlled potential electrolysis of 1 at the potential of the former wave gave the 1,1-dimethylethylamines (3) as well as the hydroxylamines 2.The amines 3 are formed exclusively from 2, probably via the O-protonated form.It is suggested that a phenyl group at the 2-position facilitates the reduction of 2 to 3 by enhancing the adsorption of 2 at the mercury cathode and that a hydroxyl group, while it interferes with the adsorption, assists the reduction by intramolecular hydrogen-bonding to stabilize the O-protonated form of 2.Keywords - tertiary nitroalkane; alkylhydroxylamine; electrochemical reduction; polarography; controlled potential electrolysis.
Oxidation of Hydroxylamine Derivatives. VI. Anodic Oxidation of N-Alkyl-β-hydroxyhydroxylamines in Aqueous Buffer Solution
Ozaki, Shigeko,Nishiguchi, Susumu,Masui, Masaichiro
, p. 2609 - 2616 (2007/10/02)
Anodic oxidation of N-alkylhydroxylamines with and without a β-hydroxy group was studied by cyclic voltammetry and controlled potential electrolysis in aqueous buffer solution of pH 8.8.The hydroxylamines with a β-hydroxy group were oxidized initially to the corresponding nitroxides and gave the final products via two routes; i) cleavage of the (α)C-(β)C bond to give aldehydes and oximes, and ii) disproportionation of the nitroxides to form the nitroso compounds.The hydroxylamines without a β-hydroxy group did not undergo cleavage of the (α)C-(β)C bond and gave nitroso compounds.Substituents on the α and β carbons affected the product distribution.When a phenyl group or two methyl groups were present on the (β)C, or one methyl group was present on both (α)C and (β)C, (α)C-(β)C bond cleavage was predominant. Keywords - N-alkyl-β-hydroxyhydroxylamine; anodic oxidation; C-C bond fission; C-nitroso compound; aldehyde; oxime; azoxy compound
