Investigation of electrochemically induced conjugate addition reaction: A facile approach to preparation of Schonberg adduct

Nematollahi, Davood; Tammari, Esmail; Esmaili, Roya

doi:10.1016/j.jelechem.2008.04.027

Cited by 26 publications

(21 citation statements)

References 20 publications

(21 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…When the sweep rate is increased, cathodic peak C 1 appears and its height increases progressively with the scan rate. In this figure, peak A 2 corresponds to oxidation of product [11], and curve c is the voltammogram of 4. The observed anodic peak in curve c is due to oxidation of 4 [15].…”

Section: Electrochemical Study Of 34-dihydroxybenzaldehyde (1)mentioning

confidence: 99%

“…E-mail: nemat@basu.ac.ir motivated us to synthesize a number of them using a facile electrochemical method recently [11]. The purpose of this work is the development of a procedure for synthesis of some new C-phosphoniumquinol betaines based upon the electrooxidation of dihydroxybenzoic acids and dihydroxybenzaldehyde in the presence of triphenylphosphine as a nucleophile on the one hand, and the estimation of the observed homogeneous rate constants (k obs ) for the reaction of electrochemically generated benzoquinones with this nucleophile by digital simulation of cyclic voltammograms, on the other hand.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Kinetics study of electrochemically induced michael reaction of benzoquinones with triphenylphosphine

Nematollahi

Esmaili

2010

JICS

Self Cite

View full text Add to dashboard Cite

The electrochemical oxidation of 3,4-dihydroxybenzaldehyde (1), 3,4-dihydroxybenzoic acid (2) and 2,5-dihydroxybenzoic acid (3) were studied in the presence of triphenylphosphine (4) as a nucleophile using cyclic voltammetry and controlled-potential coulometry. The results indicate that the quinones derived from oxidation of 3,4-dihydroxybenzaldehyde, 3,4-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid participate in Michael addition reaction with triphenylphosphine (4). In this work, based on an EC mechanism, the observed homogeneous rate constants (k obs ) of the reaction of produced benzoquinones with triphenylphosphine (4) were estimated by comparing the experimental cyclic voltammograms with the digitally simulated results.

show abstract

Section: Electrochemical Study Of 34-dihydroxybenzaldehyde (1)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Kinetics study of electrochemically induced michael reaction of benzoquinones with triphenylphosphine

Nematollahi

Esmaili

2010

JICS

Self Cite

View full text Add to dashboard Cite

show abstract

“…1, curve a). [2][3][4][5][6][7][8][9][10][11] The electrooxidation of catechol (1a) in the presence of phenyl-Meldrum's acid (3) was studied in some detail. Fig.…”

Section: Resultsmentioning

confidence: 99%

“…1) In this connection, in order to synthesis catechol derivatives, we studied the electrochemical oxidation of benzenediols in the presence of CH acid nucleophiles, [2][3][4] SH acid nucleophiles, [5][6][7][8][9] nitrite ion 10) and triphenylphosphine. 11) Also, it is demonstrated that, in comparison with simple catechols, the "highly oxygenated compounds with catechol ring" exhibit interesting biological activities. 12,13) Therefore, the development of a simple synthetic route for the synthesis of "highly oxygenated compounds with catechol ring" from readily available reagents is one of the major tasks.…”

mentioning

confidence: 99%

Electrochemical Oxidation of Catechols in the Presence of Phenyl-Meldrum's Acid. Synthesis and Kinetic Evaluation

Nematollahi

Bamzadeh

Shayani‐Jam

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

23Catechol, by itself, and mono-substituted catechols are active in part against Pseudomonas, Bacillus, but not Penicillium species. Many flavonoids and catechol derivatives turned out to be as antimicrobial agents. 1) In this connection, in order to synthesis catechol derivatives, we studied the electrochemical oxidation of benzenediols in the presence of CH acid nucleophiles, 2-4) SH acid nucleophiles, 5-9) nitrite ion 10) and triphenylphosphine. 11) Also, it is demonstrated that, in comparison with simple catechols, the "highly oxygenated compounds with catechol ring" exhibit interesting biological activities.12,13) Therefore, the development of a simple synthetic route for the synthesis of "highly oxygenated compounds with catechol ring" from readily available reagents is one of the major tasks. In this direction, we recently reported the synthesis of some "highly oxygenated compounds with catechol ring." 14) This idea prompted us to investigate the electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile and represents a facile and one-pot electrochemical method for the synthesis of some new "highly oxygenated compounds with catechol ring." Also, an additional purpose of this work is the kinetic and mechanistic study of the electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid and the estimation of the observed homogeneous rate constants (k obs ) of reaction of electrochemically generated o-benzoquinones with this nucleophile by digital simulation of cyclic voltammograms. Results and DiscussionElectrochemical Investigations The cyclic voltammogram of 1.0 mM catechol (1a) in aqueous solution containing 0.2 M acetate buffer (pHϭ5.0) shows one anodic peak (A 1 ) and the corresponding cathodic peak which correspond to the transformation of catechol (1a) to o-benzoquinone (2a) and vice-versa, within a quasi-reversible two electron process (Fig. 1, curve a).2-11) The electrooxidation of catechol (1a) in the presence of phenyl-Meldrum's acid (3) was studied in some detail. Fig. 1, curve b, shows the first cyclic voltammogram obtained for a 1.0 mM solution of 1a in the presence of 0.1 mM phenyl-Meldrum's acid (3). The voltammogram exhibits one anodic peak (A 1 ) and one cathodic peak (C 1 ) that shows decreasing in comparison to the cathodic peak of catechol (1a) in the absence of 3. In this figure, curve c is the voltammogram of 3 in the absence of 1a.The effect of potential sweep rate on shape of cyclic voltammograms of catechol (1a) in the presence of phenylMeldrum's acid (3) was studied, too. It is seen that, proportional to the augmentation of the potential sweep rate, the height of peak C 1 increases. A similar situation is observed when the 3 to 1a concentration ratio is decreased. A plot of the peak current ratio (I pC1 /I pA1 ) versus the scan rate for a mixture of catechol (1a) and phenyl-Meldrum's acid (3) confirms the reactivity of o-benzoquinone (2a) toward phenylMeldrum's acid (3), appearing as an increase in the peak cur- Electrochemic...

show abstract

“…The synthesis of modifier, 4-Hydroxy-2-(triphenylphosphonio) phenolate (HTP), was done based on Ref. 18 .…”

Section: Instrumentationmentioning

confidence: 99%

Differential Pulse Voltammetry Technique for the Determination of Imipramine, Dopamine and Norepinephrine Using a Hydroquinone Derivative Multi-wall Carbon Nano-tube Carbon Paste Electrode

Shishehbore¹,

Vafai-Shahi²,

Shefaie³

et al. 2017

Orient. J. Chem

View full text Add to dashboard Cite

In this study, a synthetic para dihydroxy benzene derivative was used for electro-catalytic determination of chemical and biological species. The modified electrode was fabricated using graphite powder, multi-wall carbon nano tubes and the synthetic compound. The analytes including imipramine, dopamine and norepinephrine were quantitied. The kinetic parameters were calculated. Based on the obtained results, the modified electrode shifted the electro-catalytic oxidation potential about 490 mV for imipramine. Analytical parameters including the limit of detection and linear dynamic range were determined using differential pulse voltammetry technique. Simultaneous determination of imipramine, norepinephrine and dopamine along with the individual determination of imipramin were studied. The method applied in urine sample with satisfactory results.

show abstract

Investigation of electrochemically induced conjugate addition reaction: A facile approach to preparation of Schonberg adduct

Cited by 26 publications

References 20 publications

Kinetics study of electrochemically induced michael reaction of benzoquinones with triphenylphosphine

Kinetics study of electrochemically induced michael reaction of benzoquinones with triphenylphosphine

Electrochemical Oxidation of Catechols in the Presence of Phenyl-Meldrum's Acid. Synthesis and Kinetic Evaluation

Differential Pulse Voltammetry Technique for the Determination of Imipramine, Dopamine and Norepinephrine Using a Hydroquinone Derivative Multi-wall Carbon Nano-tube Carbon Paste Electrode

Contact Info

Product

Resources

About