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Synthesis of nitrocyclopropanedicarboxylic acid derivatives by addition of α-bromonitroalkanes to methylidene malonic, methylidene cyanoacetic or maleic acid derivatives

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Abstract

A potassium carbonate promoted addition of 2-bromonitroalkanes to methylidenemalonic and methylidenecyanoacetic acid derivatives and N-benzylmaleimide leads to the functionalized nitrocyclopropanes. In the case of less active olefins, it is reasonable to use the phase-transfer catalyst Bu4NPF6 (10 mol.%), whereas in the case of N-benzylmaleimide, to carry out the process in the ionic liquid [bmim]BF4.

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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

    G. V. Kryshtal, G. M. Zhdankina, A. S. Shashkov & S. G. Zlotin

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  1. G. V. Kryshtal
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  2. G. M. Zhdankina
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  3. A. S. Shashkov
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  4. S. G. Zlotin
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Correspondence to S. G. Zlotin.

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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2237–2243, November, 2011.

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Kryshtal, G.V., Zhdankina, G.M., Shashkov, A.S. et al. Synthesis of nitrocyclopropanedicarboxylic acid derivatives by addition of α-bromonitroalkanes to methylidene malonic, methylidene cyanoacetic or maleic acid derivatives. Russ Chem Bull 60, 2279–2285 (2011). https://doi.org/10.1007/s11172-011-0348-8

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  • DOI: https://doi.org/10.1007/s11172-011-0348-8

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