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Unusual transformation of 3-alkylfuroxans into 3-(nitrooxyalkyl)furoxans on treatment with a mixture of nitric and sulfuric acids

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Abstract

A versatile one-pot synthesis of 4-substituted 3-(nitrooxyalkyl)furoxans by the reaction of 3-alkylfuroxans with a mixture of nitric and sulfuric acids was developed. A plausible mechanism of this unusual transformation was explained in terms of a new Grob-type fragmentation.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. A. Ogurtsov, S. G. Zlotin & O. A. Rakitin

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    A. V. Shastin

Authors
  1. V. A. Ogurtsov
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  2. A. V. Shastin
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  3. S. G. Zlotin
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  4. O. A. Rakitin
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Correspondence to V. A. Ogurtsov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2901–2906, December, 2016.

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Ogurtsov, V.A., Shastin, A.V., Zlotin, S.G. et al. Unusual transformation of 3-alkylfuroxans into 3-(nitrooxyalkyl)furoxans on treatment with a mixture of nitric and sulfuric acids. Russ Chem Bull 65, 2901–2906 (2016). https://doi.org/10.1007/s11172-016-1675-6

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  • DOI: https://doi.org/10.1007/s11172-016-1675-6

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