General and Simple Method for the Synthesis of 3-nitroformazan Using Arenediazonium Tosylates

Author(s): Pavel V. Petunin, Rashid R. Valiev, Rodion G. Kalinin, Marina E. Trusova, Viktor V. Zhdankin, Pavel S. Postnikov

Journal Name: Current Organic Synthesis

Volume 13 , Issue 4 , 2016


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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.

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Article Details

VOLUME: 13
ISSUE: 4
Year: 2016
Page: [623 - 628]
Pages: 6
DOI: 10.2174/1570179413666160205002843
Price: $65

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