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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Research Article

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 and Pavel S. Postnikov

Volume 13, Issue 4, 2016

Page: [623 - 628] Pages: 6

DOI: 10.2174/1570179413666160205002843

Price: $65

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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