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Halogenation of Aldoximes. A Versatile Reaction for the Synthesis of Highly Functionalized Hydroximoyl Chlorides and Furazan N-Oxides

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Abstract

Halogenation of aromatic aldoximes with N-chlorosuccinimide under mild conditions produced a variety of highly functionalized compounds, including the corresponding hydroximoyl chlorides and furazan N-oxides. In some cases, the reaction was accompanied by chlorination of the aromatic ring. The initial aldoximes were prepared from substituted benzaldehydes and hydroxylamine hydrochloride. The structure of some of the synthesized compounds was determined by X-ray analysis.

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ACKNOWLEDGMENTS

AHC thanks CONACYT and VIEP-BUAP for scholarships.

Funding

This work was supported by VIEP-BUAP grant (project ARCS-NAT16-G).

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Authors and Affiliations

  1. Centro de Química del Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Puebla, Mexico

    A. Hernández-Calva, M. Arroyo-Carranza & A. Ramírez-Monroy

  2. Departamento de Química Inorgánica, Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, 72570, Puebla, Puebla, Mexico

    L. Meléndez-Balbuena

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  1. A. Hernández-Calva
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  2. L. Meléndez-Balbuena
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  3. M. Arroyo-Carranza
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  4. A. Ramírez-Monroy
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Correspondence to M. Arroyo-Carranza or A. Ramírez-Monroy.

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Hernández-Calva, A., Meléndez-Balbuena, L., Arroyo-Carranza, M. et al. Halogenation of Aldoximes. A Versatile Reaction for the Synthesis of Highly Functionalized Hydroximoyl Chlorides and Furazan N-Oxides. Russ J Org Chem 59, 2221–2229 (2023). https://doi.org/10.1134/S1070428023120217

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