General and simple method for the synthesis of 3-nitroformazan using arenediazonium tosylates

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Abstract

A general and simple procedure for the synthesis of 3-nitroformazan using arenediazonium tosylates was developed. This convenient procedure can be applied for the preparation of 3-nitroformazans containing electron-donating or electron-withdrawing groups. First the anomaly 1,5-bis(4-methoxyphenyl)-3-nitroformazan was synthesized as the mixture of TSSC (trans-syn, s-cis) and previously unknown for 3-nitroformazans TASC (transanti, s-cis) isomers. The structure and spectral characteristics of TASC isomer were explained using quantumchemical calculation with TDDFT/B3LYP/6-31++G(d,p) level of theory.

Original languageEnglish
Pages (from-to)623-628
Number of pages6
JournalCurrent Organic Synthesis
Volume13
Issue number4
Publication statusPublished - 1 Aug 2016

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Isomers
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Keywords

  • Arenediazonium tosylates
  • Azo-coupling
  • Diazonium salts
  • Formazans
  • Quantum-chemical calculations
  • TDDFT

ASJC Scopus subject areas

  • Organic Chemistry
  • Biochemistry

Cite this

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abstract = "A general and simple procedure for the synthesis of 3-nitroformazan using arenediazonium tosylates was developed. This convenient procedure can be applied for the preparation of 3-nitroformazans containing electron-donating or electron-withdrawing groups. First the anomaly 1,5-bis(4-methoxyphenyl)-3-nitroformazan was synthesized as the mixture of TSSC (trans-syn, s-cis) and previously unknown for 3-nitroformazans TASC (transanti, s-cis) isomers. The structure and spectral characteristics of TASC isomer were explained using quantumchemical calculation with TDDFT/B3LYP/6-31++G(d,p) level of theory.",
keywords = "Arenediazonium tosylates, Azo-coupling, Diazonium salts, Formazans, Quantum-chemical calculations, TDDFT",
author = "Petunin, {Pavel Vasilievich} and Valiev, {Rashid R.} and Kalinin, {Rodion G.} and Trusova, {Marina E.} and Zhdankin, {Viktor Vladimirovich} and Postnikov, {Pavel S.}",
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T1 - General and simple method for the synthesis of 3-nitroformazan using arenediazonium tosylates

AU - Petunin, Pavel Vasilievich

AU - Valiev, Rashid R.

AU - Kalinin, Rodion G.

AU - Trusova, Marina E.

AU - Zhdankin, Viktor Vladimirovich

AU - Postnikov, Pavel S.

PY - 2016/8/1

Y1 - 2016/8/1

N2 - A general and simple procedure for the synthesis of 3-nitroformazan using arenediazonium tosylates was developed. This convenient procedure can be applied for the preparation of 3-nitroformazans containing electron-donating or electron-withdrawing groups. First the anomaly 1,5-bis(4-methoxyphenyl)-3-nitroformazan was synthesized as the mixture of TSSC (trans-syn, s-cis) and previously unknown for 3-nitroformazans TASC (transanti, s-cis) isomers. The structure and spectral characteristics of TASC isomer were explained using quantumchemical calculation with TDDFT/B3LYP/6-31++G(d,p) level of theory.

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