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Synthesis of various cyclopropyl methyl bromide and its derivatives from ketones and/or aldehydes and some β-dicarbonyl compounds in the presence of BrCN and Et3N

  • Saeed Gholizadeh
  • Kazem D. SafaEmail author
  • Nader Noroozi Pesyan
Original Paper
  • 9 Downloads

Abstract

The ultimate goal in this paper has been developed for the synthesis of structurally various bromomethyl cyclopropane via an α-bromoketone and/or aldehydes with ethyl cyanoacetate or malononitrile and cyanogen bromide (BrCN) in the presence of Et3N to give products in excellent yields within about 3 s. All structures were characterized by IR, 1H-NMR, 13C-NMR, and Mass spectroscopy techniques. The reaction mechanism was discussed.

Keywords

Ethyl cyanoacetate One-pot reaction 3-Alkyl-3-(bromomethyl)-1,2-dipropionylcyclopropane-1,2-dicarbonitrile 3-(4-(Bromomethyl)phenyl)cyclopropane-1,1,2,2-tetracarbonitrile Cyanogen bromide N-Bromosuccinimide Photochemical Bromonium ion 

Notes

Acknowledgements

We gratefully acknowledge the financial support by the Research Council of the University of Tabriz. The Pakshoo company supported this work is much appreciated.

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Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  • Saeed Gholizadeh
    • 1
  • Kazem D. Safa
    • 1
    Email author
  • Nader Noroozi Pesyan
    • 2
  1. 1.Organosilicon Research Laboratory, Faculty of ChemistryUniversity of TabrizTabrizIran
  2. 2.Department of Organic Chemistry, Faculty of ChemistryUrmia UniversityUrmiaIran

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