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Reactions of a hydroximic acid chloride-a 3-imidazoline 3-oxide derivative-with nitrogen-containing nucleophilic reagents and preparation of stable amidoxime N-oxyl radicals

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A hydroximic acid chloride, viz., 4-chloroximino-3-imidazoline 3-oxide, reacts with nitrogen-containing nucleophilic reagents to give amidoxime derivatives. The reaction with tert-butylhydroxylamine leads to an N-hydroxyamidoxime, the oxidation of which made it possible to preparatively isolate an amidoxime N-oxyl radical, viz., 4-(N-oxyl-N-tert-butylcarboxamidoximino)-1,2,2,5,5-pentamethyl-3-imidazoline 3-oxide.

  2. 2.

    Oxidation of the radical gives a nitroso nitrone, and alkylation gives only an O-alkylation product (an ether amidoxime N-oxyl), whereas the similarly constructed amidoxime reacts to give both an O-alkylation product (an ether amidoxime) and an N-alkylation product (a nitrone).

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Authors and Affiliations

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

    V. V. Martin, L. A. Vishnivetskaya, I. A. Grigor'ev, S. A. Dikanov & L. B. Volodarskii

  2. Institute of Chemical Kinetics and Combustion, Siberian Branch, Academy of Sciences of the USSR, Novosibirsk

    V. V. Martin, L. A. Vishnivetskaya, I. A. Grigor'ev, S. A. Dikanov & L. B. Volodarskii

Authors
  1. V. V. Martin
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  2. L. A. Vishnivetskaya
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  3. I. A. Grigor'ev
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  4. S. A. Dikanov
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  5. L. B. Volodarskii
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1616–1623, July, 1985.

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Martin, V.V., Vishnivetskaya, L.A., Grigor'ev, I.A. et al. Reactions of a hydroximic acid chloride-a 3-imidazoline 3-oxide derivative-with nitrogen-containing nucleophilic reagents and preparation of stable amidoxime N-oxyl radicals. Russ Chem Bull 34, 1477–1484 (1985). https://doi.org/10.1007/BF00950152

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  • DOI: https://doi.org/10.1007/BF00950152

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