Arylations mediated by lead(IV) in the presence of formazan and imine ligands

Iqbal, Amjid; Moloney, Mark G.; Siddiqui, Hamid Latif; Thompson, Amber L.

doi:10.1016/j.tetlet.2009.05.086

Cited by 3 publications

(2 citation statements)

References 27 publications

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“…Interestingly, 3,5-diphenyl-1-(4-bromophenyl)formazan (regioisomer of 1, CCDC code EMEVUO; Tunç & Yıldırım, 2010) shows alternating bond lengths, which reflects the fact that the two nitrogen atoms are chemically inequivalent in this molecule. An example with split hydrogen positions is 1,5-diphenyl-3-(p-nitrophenyl)formazan (GUHCIW; Iqbal et al, 2009), which shows a similar stacking to that observed in 1 and can be formally derived from 1 by replacing the bromine with a nitro group. 33 examples for 1,3,5-aryl-substituted verdazyls were found in the CSD, only 14 of them Kuhn-verdazyls.…”

Section: Database Surveymentioning

confidence: 97%

Syntheses, spectroscopy, and crystal structures of 3-(4-bromophenyl)-1,5-diphenylformazan and the 3-(4-bromophenyl)-1,5-diphenylverdazyl radical and the crystal structure of the by-product 5-anilino-3-(4-bromophenyl)-1-phenyl-1H-1,2,4-triazole

Schnakenburg

Meyer

2018

Acta Cryst E

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Section: Database Surveymentioning

confidence: 97%

Syntheses, spectroscopy, and crystal structures of 3-(4-bromophenyl)-1,5-diphenylformazan and the 3-(4-bromophenyl)-1,5-diphenylverdazyl radical and the crystal structure of the by-product 5-anilino-3-(4-bromophenyl)-1-phenyl-1H-1,2,4-triazole

Schnakenburg

Meyer

2018

Acta Cryst E

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“…1 Numerous studies have been undertaken related to their syntheses, structural and spectroscopic properties, [2][3][4][5] photochemical transformations, 6,7 tautomer formation, 8,9 the synthesis of crown formazans 10 and the broad spectrum of biological activities. [11][12][13][14][15] In addition, formazan derivatives were reported to be used for the synthesis, optical properties, and the electrochemical behaviours of metal [16][17][18][19][20] and boron complexes as functional materials. [21][22][23] Formazans form tetrazolium salt upon oxidation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure, optical and electrochemical properties of novel diphenylether-based formazan derivatives

2015

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In this study, formazans 5a-5h were synthesized by coupling the reactions of substituted phenylhydrazone compounds 3a-3h with diazonium salt of 4-chloro-2-phenoxybenzenamine (4). The substituted phenylhydrazones 3a-3h were obtained from the condensation of substituted phenylhydrazines 1a-1h with 4-methoxybenzaldehyde (2). The structures of the formazans were characterized by using elemental analysis, FTIR, 1 H NMR, 13 C NMR, LC-MS and the crystal structure of compound 5e was determined by X-ray crystallography. The absorption spectra of all compounds were investigated in various solvents. Although their absorption bands are only slightly dependent on the polarities of solvents, the significant change was observed by altering the electronic characteristics of the substituents. The fluorescence quantum yield properties and Stokes shifts of compounds 5a-5h in DMSO were also explored. Electrochemical properties of the new products were studied by CV measurements. In addition, computational studies were conducted at the PBE1PBE/6-311g (2d,2p) level to shed light on the structures of possible tautomers and intramolecular H-bonds.Scheme 1 Synthetic route for the formation of formazan derivatives 5a-5h.Scheme 2 Intramolecular hydrogen bonding and tautomerisation of the formazan system. View Article Onlinea Oxidation and reduction potentials from cyclic voltammograms. b Onsets of oxidation and reduction. c HOMO = À(E onset (ox) + 4.4) (eV), LUMO = À(E onset (red) + 4.4).Scheme 4 (a) Schematic representation of the structure of 5c for possible oxidation mechanisms of 5c, 5d, 5g and 5h; (b) structure of 5a for possible oxidation mechanism of 5a, 5b, 5e and 5f.

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Novel formazan derivatives containing phenylsulfanyl and carbonyl units: synthesis, optical and electrochemical properties

Turkoglu

Berber

2016

RSC Adv.

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Arylations mediated by lead(IV) in the presence of formazan and imine ligands

Cited by 3 publications

References 27 publications

Syntheses, spectroscopy, and crystal structures of 3-(4-bromophenyl)-1,5-diphenylformazan and the 3-(4-bromophenyl)-1,5-diphenylverdazyl radical and the crystal structure of the by-product 5-anilino-3-(4-bromophenyl)-1-phenyl-1H-1,2,4-triazole

Syntheses, spectroscopy, and crystal structures of 3-(4-bromophenyl)-1,5-diphenylformazan and the 3-(4-bromophenyl)-1,5-diphenylverdazyl radical and the crystal structure of the by-product 5-anilino-3-(4-bromophenyl)-1-phenyl-1H-1,2,4-triazole

Synthesis, crystal structure, optical and electrochemical properties of novel diphenylether-based formazan derivatives

Novel formazan derivatives containing phenylsulfanyl and carbonyl units: synthesis, optical and electrochemical properties

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