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Synthesis of α-cyano hydroxylamines via three-component reactions and its computational mechanistic study

  • Mohammad A. Ranjbari
  • Hossein TavakolEmail author
Article
  • 17 Downloads

Abstract

In the present report, various α-cyano hydroxylamines were synthesized via a 3-component reaction between aromatic aldehydes, phenylhydroxylamine and trimethylsilyl cyanide at room temperature. In this line, several solvents and catalysts were employed to obtain the best conditions for the reaction. Among the employed solvents and catalysts, methanol (as solvent) and NiCl2 (as catalyst) showed the highest performances. Moreover, the mechanistic details for the both steps of this reaction in the gas phase and explicit solvent (methanol) model have been studied using DFT calculations and the energy profiles for all steps were obtained. The results of these computations are in agreement with the experimental results, which showed the methanol is the best solvent and NiCl2 is the most appropriate catalyst for this reaction.

Keywords

α-Cyano hydroxylamine Strecker Nitrone Mechanism Catalyst DFT 

Notes

Acknowledgements

We acknowledge the Institute of organic chemistry, University of Innsbruck (UIBK) for providing NMR facility. We have special thanks to Professor Ronald Micura (the head of the institute) and Professor Christoph Kreutz for their valuable assistances.

Compliance with ethical standards

Conflicts of interest

The authors declare no competing financial interests.

Supplementary material

11144_2019_1688_MOESM1_ESM.docx (2.3 mb)
Supplementary material 1 (DOCX 2341 kb)

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Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2019

Authors and Affiliations

  1. 1.Department of ChemistryIsfahan University of TechnologyIsfahanIran

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