Electrochemical Behaviour of Hydrazonates in Protic and Aprotic Medium

Saied, Taieb; Benkhoud, Mohamed Lamine; Boujlel, Khaled

doi:10.1081/scc-120002006

Cited by 9 publications

(8 citation statements)

References 8 publications

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“…The electrochemical reduction of 2 in CH 2 Cl 2 (Figure , curve 3) or acetonitrile is a quasireversible process (Table ). These reduction potentials are in good agreement with the literature data for related systems . The formed radical anion is unstable and can be protonated readily (i.e., by the neutral catechol 2 ).…”

Section: Resultssupporting

confidence: 90%

Tin(IV) and Antimony(V) Complexes Bearing Catecholate Ligands Connected to Ferrocene – Syntheses, Molecular Structures, and Electrochemical Properties

et al. 2016

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The ferrocenyl‐containing 3,5‐di‐tert‐butylcatechol Fc‐L‐CatH2 (2) was synthesized by the condensation of the precursor 6‐(hydrazonomethyl)‐3,5‐di‐tert‐butylcatechol 6‐(H2N–N=CH)CatH2 (1) with ferrocenecarboxaldehyde (L = –CH=N–N=CH–, Cat = 3,5‐di‐tert‐butylcatecholate, Fc = ferrocene). The exchange reaction between catechol 2 and Ph3SbBr2 in the presence of a base (Et3N) in toluene leads to the formation of the triphenylantimony(V) catecholate (Fc‐L‐Cat)SbPh3 (3) as the main product and the ionic bromotriphenylantimony(V) catecholate (Fc‐LH‐Cat)SbPh3Br (4) containing a hydraziniumylidene cation (LH = –CH=NH+–N=CH–) as the byproduct. The change of toluene to tetrahydrofuran (THF) results in the formation of 4 as the main product in nearly quantitative yield. The exchange reactions of catechol 2 with Ph2SnCl2 and SnCl4 give anionic catecholate complexes bridged with hydraziniumylidene cations even in the presence of excess base. Complexes (Fc‐LH‐Cat)SnPh2Cl (5), (Fc‐LH‐Cat)2SnPh2 (6), and (Fc‐LH‐Cat)2SnCl2 (7) were synthesized. The compounds obtained were characterized by IR spectroscopy, 1H and 13C NMR spectroscopy, elemental analysis, and cyclic voltammetry. The molecular structures of crystals of 5–7 were determined by X‐ray diffraction analysis. The formation of catecholates 4–7 with hydraziniumylidene cations is caused by intramolecular hydrogen bonding between the hydroxy and imine groups, which leads to proton transfer from the oxygen atom to the nitrogen atom of the hydrazine linker.

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Section: Resultssupporting

confidence: 90%

Tin(IV) and Antimony(V) Complexes Bearing Catecholate Ligands Connected to Ferrocene – Syntheses, Molecular Structures, and Electrochemical Properties

et al. 2016

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“…The resulting mixture was hydrolyzed by a saturated solution of NaHCO 3 , if electrolysis is carried out in absence of pyridine, and extracted three times with 50 mL of ether. However in presence of pyridine, the mixture obtained after removal of solvent was hydrolyzed by a saturated solution of NH 4 Cl and then extracted. The organic phases were washed by small amounts of water and dried over magnesium sulfate (MgSO 4 ).…”

Section: Chemicals and Solutionsmentioning

confidence: 99%

“…The chemistry of N-functional derivatives such as N-acylamido and thioamidoimidates [1][2][3], hydrazonates [4], N-2 acyl and ethoxycarbonyl benzimidazone imidates [5], Nnitrophenyl imidates [6], has attracted an increasing amount of attention in recent years owing to the intrinsic interest in their structures and their wide application in organic and electrochemical synthesis. In this context, several studies devoted to the synthesis of heterocyclic compounds by electrochemical reduction and oxidation of several N-functional derivatives cited above are reported herein.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical synthesis of 1,2,4-triazol-3-thione derivatives: Anodic oxidation of N-thioamidohydrazones

Chmekh

Tapsoba

Medini

et al. 2007

Journal of Electroanalytical Chemistry

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“…Quantitative results for preparative electrolysis run in the presence of proton donor showed the occurance of reductive cleavage of the N-N bond giving imines 131 and iminoethers 132 in good yield [90]. Quantitative results for preparative electrolysis run in the presence of proton donor showed the occurance of reductive cleavage of the N-N bond giving imines 131 and iminoethers 132 in good yield [90].…”

Section: Electrolytic Reductionmentioning

confidence: 99%

The Chemistry of Hydrazonates

Shawali¹,

Sherif

2007

COC

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The chemistry of esters of hydrazonoic acids has gained increased interest in both synthetic organic chemistry and biological fields. Since a large number of developments in the use of such esters, a review of such developments, covering the literature up to mid 2005, seems to be of considerable value. The present review presents their structural features, nomenclature, synthetic methods and chemical reactions. The utility of the latter reactions for synthesis of various heterocyclic ring systems including mono-, bi-, tri-, tetra-, and penta-heterocycles. In addition, their silicon chelates and biological applications are presented.

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Electrochemical Behaviour of Hydrazonates in Protic and Aprotic Medium

Cited by 9 publications

References 8 publications

Tin(IV) and Antimony(V) Complexes Bearing Catecholate Ligands Connected to Ferrocene – Syntheses, Molecular Structures, and Electrochemical Properties

Tin(IV) and Antimony(V) Complexes Bearing Catecholate Ligands Connected to Ferrocene – Syntheses, Molecular Structures, and Electrochemical Properties

Electrochemical synthesis of 1,2,4-triazol-3-thione derivatives: Anodic oxidation of N-thioamidohydrazones

The Chemistry of Hydrazonates

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