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Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 2, pp 353–362 | Cite as

Aliphatic nitro compounds chemistry: oximes–nitrones tunable production through directed tandem synthesis

  • Foad KazemiEmail author
  • Moosa Ramdar
  • Jamal Davarpanah
Original Paper
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Abstract

Reduction of aliphatic nitro compounds in the presence of aldehydes and dialdehydes for tunable directed synthesis of oximes, nitrones, nitrone–oximes, and dinitrones was reported. The slow and nonselective reduction of aliphatic nitro compounds was directed by condensation of in situ prepared alkylhydroxylamines with aromatic aldehydes. Mononitrones and dinitrones were synthesized at reflux and at 55 °C conditions, respectively, in tetrahydrofuran using SnCl2·2H2O and Na2CO3. It was found that the presence of a catalytic amount of carboxylic acid such as 3-phenylpropanoic acid increases the yield of dinitrones versus nitrone–oxime and dioxime when dialdehydes were used as aldehyde source.

Graphical abstract

Keywords

Aliphatic nitro Oxime Nitrone Nitrone–oxime Dinitrone 
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Notes

Acknowledgements

This work was supported by Institute for Advanced Studies in Basic Sciences (IASBS).

Supplementary material

706_2018_2326_MOESM1_ESM.pdf (8.9 mb)
Supplementary material 1 (PDF 9110 kb)

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of ChemistryInstitute for Advanced Studies in Basic Sciences (IASBS)ZanjanIran
  2. 2.Center for Climate and Global Warming (CCGW)Institute for Advanced Studies in Basic Sciences (IASBS)ZanjanIran
  3. 3.Chemistry DepartmentProduction Technology Research Institute-ACECRAhvazIran

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