Electrochemical oxidation of catechols in the presence of acetylacetone

Mechanistic Study of Electrochemical Oxidation of 2,5-Dihydroxybenzoic Acid and 3,4-Dihydroxybenzaldehyde in the Presence of 3-Hydroxy-1H-phenalene-1-one

“…All anodic and cathodic peaks disappear when the charge consumption becomes about 4e Ϫ per molecule of 1b. Our experiences on electrochemical oxidation of catechols in the presence of nucleophiles, [12][13][14][15][16][17][19][20][21] diagnostic criteria of cyclic voltammetry, consumption of four electrons per molecule of 1b and the mass spectra of isolated product (m/z, 330), indicate that the reaction mechanism of electrooxidation of 1b in the presence of 3 is ECEC (Chart 3).…”

“…8) They are also potent and selective oxytocin antagonists, 9) PDE5 inhibitor for treatment of erectile dysfunction, 10) and H 3 receptor antagonists.11) In order to synthesise new quinone derivatives we studied the electrochemical oxidation of benzenediols in the presence of a variety of nucleophiles.12,13) Also, in order to synthesise benzofuran derivatives we investigated the electrochemical oxidation of catechols in the presence of b-diketones such as acetylacetone, 14) dimedone, 15) and dibenzoylmethane. 16) In this connection, the electrochemical oxidation of hydroquinones and catechols in the presence of 3-hydroxy-1H-phenalene-1-one (3) as a nucleophile has been recently reported by us (Chart 1).…”

“…12,13) Also, in order to synthesise benzofuran derivatives we investigated the electrochemical oxidation of catechols in the presence of b-diketones such as acetylacetone, 14) dimedone, 15) and dibenzoylmethane. 16) In this connection, the electrochemical oxidation of hydroquinones and catechols in the presence of 3-hydroxy-1H-phenalene-1-one (3) as a nucleophile has been recently reported by us (Chart 1).…”

A New Way for Synthesis of Phenoxazine and Diphenoxazine Derivatives via Electrochemical Method

“…A peak current ratio (I p C1 /I p A1 ) of nearly unity, particularly during the repetitive cycling of potentials may be considered as a criterion for the stability of p-quinone produced at the surface of the electrode under experimental condition. In other words, any hydroxylation [17][18][19][20][21][22] or dimerization [23][24][25] reaction is too slow to be observed on the cyclic voltammetry time-scale.…”

Cyclic voltammetry for a preliminary study of appropriate electro-synthesis reactions of naphthalene derivatives

“…In the above paper, experimental data of CV oxidation of catechol, presented in a paper by D. Nematollahi It follows from more recent papers [1][2][3] concerning CV oxidation of catechol, that our earlier estimation may need to be increased by about 30-70%. The proposed change may be understood, taking into account that catechol seems easily oxidizable in air, especially when dissolved.…”