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Formation of furoxans and 1,2-diazetine 1,2-dioxides by oxidation of α-hydroxylamino oximes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The oxidation of secondary and tertiaryα-hydroxylamino oximes with sodium hypobromite gives, respectively, furoxans and 3-bromo-1,2-diazetine 1,2-dioxides. The intermediate oxidation products, which confirm the proposed reaction mechanism, were isolated. When 3-bromo-1,2-diazetine 1,2-dioxides are heated in benzene, the ring opens with the evolution of nitrogen oxides and the formation of halo olefins.

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Authors and Affiliations

  1. Novosbirsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR, USSR

    L. B. Volodarskii & L. A. Tikhonova

Authors
  1. L. B. Volodarskii
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  2. L. A. Tikhonova
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 748–752, June, 1975.

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Volodarskii, L.B., Tikhonova, L.A. Formation of furoxans and 1,2-diazetine 1,2-dioxides by oxidation of α-hydroxylamino oximes. Chem Heterocycl Compd 11, 649–652 (1975). https://doi.org/10.1007/BF00959952

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  • DOI: https://doi.org/10.1007/BF00959952

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