67950-95-2Relevant articles and documents
Oxidative study of gabapentin by alkaline hexacyanoferrate(III) in room temperature in presence of catalytic amount of Ru(III) - a mechanistic approach
Jose, Timy P.,Angadi, Mahantesh A.,Salunke, Manjalee S.,Tuwar, Suresh M.
, p. 121 - 124 (2008)
The kinetics of oxidation of gabapentin by hexacyanoferrate(III) in aqueous alkaline medium at a constant ionic strength of 0.5 mol dm-3 was studied spectrophotometrically. The reaction is of first order in [HCF(III)] and of less than unit order in [alkali]. The reaction rate is independent upon [gabapentin]. Effects of added products, ionic strength and dielectric constant of the reaction medium have been investigated. Oxidative product of gabapentin was identified. A suitable mechanism has been proposed. The reaction constants involved in the different steps of mechanism are calculated. The activation parameters of the mechanism are computed and discussed.
Kinetics of oxidation of gabapentin (neurontin) by chloramine-T in perchloric acid medium
Mohan,Jagadeesh
experimental part, p. 1226 - 1229 (2009/03/11)
A kinetic study of oxidation of gabapentin (neurontin) by chloramine-T has been carried out in HClO4 medium at 303 K. The reaction rate is first order dependence on [CAT]o, fractional order on [GP]o and an inverse fractional order on [H+]. Effects of added p-toluenesulfonamide and halide ions, and varying ionic strength of the medium have been investigated and the activation parameters evaluated. The reaction fails to initiate polymerization of acrylonitrile. The reaction stoichiometry and oxidation products have been identified and a suitable mechanism has been proposed.
Superoxide Anion Radical (O2-anionradical) Mediated Base Catalyzed Autooxidation of α-Keto Enols
Frimer, Aryeh A.,Gilinsky-Sharon, Pessia,Aljadeff, Gladis,Marks, Vered,Rosental, Zilpa
, p. 4866 - 4872 (2007/10/02)
Eight 4,4-disubstituted 2-hydroxycyclohexa-2,5-dien-1-ones were prepared by the base-catalysed autooxidation (BCA) of the corresponding 4,4- or 5,5-disubstituted cyclohex-2-en-1-ones.Upon reaction with superoxide anion radical (O2-anionradical, generated from KO2/18-crown-6) in inert nonpolar aprotic media at room temperature, α-keto enols 3a-g undergo initial deprotonation of the enol hydrogen followed by BCA at C3 of the resulting enolate.Aqueous acid workup of the reaction mixture yields lactols 4, while methyl iodide quenching generates methoxy lactones 5.Lactols 4 can be readily converted to their acetoxy analogues 8, opened to aldehydo methyl esters 6, or reduced to the related lactones 7.The latter suggests a convenient one-pot synthesis of 2,3-unsaturated δ-valerolactones from the corresponding cyclohex-2-en-1-ones. 4,4-Diphenyl enol 3h, by contrast, resists BCA (whether mediated by O2-anionradical or t-C4H9O-anion) to the corresponding lactol yielding instead a variety of oxidative cleavage products 13-18. 2-Hydroxyspirodec-1-en-3-one (21) also underwent O2-anionradical-mediated BCA, yielding diacids 22 and 26 as well as lactol 30.The synthetic applications of these results are also discussed.
