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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

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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.

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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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Authors and Affiliations

  1. Organosilicon Research Laboratory, Faculty of Chemistry, University of Tabriz, Tabriz, 51666-14766, Iran

    Saeed Gholizadeh & Kazem D. Safa

  2. Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, 57159, Iran

    Nader Noroozi Pesyan

Authors
  1. Saeed Gholizadeh
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  2. Kazem D. Safa
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Correspondence to Kazem D. Safa.

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Gholizadeh, S., Safa, K.D. & Noroozi Pesyan, N. 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. J IRAN CHEM SOC 16, 1239–1253 (2019). https://doi.org/10.1007/s13738-019-01600-x

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  • DOI: https://doi.org/10.1007/s13738-019-01600-x

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