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Transformations of Peroxide Products of Non-1-ene Ozonolysis by the Action of Carboxylic Acid Hydrazides

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Abstract

The behavior of aliphatic (cyclohexanecarboxylic) and aromatic (salicylic and isonicotinic) carboxylic acid hydrazides toward peroxide products of ozonolysis of a terminal alkene, non-1-ene, in protic (methanol) and aprotic solvents (THF, methylene chloride) has been studied. These hydrazides are capable of acting as reducing agents or decomposing intermediate peroxides. For the synthesis of N′-octylidene isoniazid derivative, it is advisable to carry out the reaction in methanol, whereas the use of THF as solvent favors formation of N′-octylidenecyclohexane-1-carbonydrazide. Salicylic acid hydrazide showed a low efficiency; in this case, mixtures of the corresponding hydrazone with octanoic acid or its methyl ester were formed in a low yield.

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ACKNOWLEDGMENTS

This study was performed using the facilities of the Chemistry joint center (Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences).

Funding

This study was financially supported by the program of the Russian Academy of Sciences “Fundamentals of Chemistry” (project no. 8, “Chemo-, Regio-, and Stereoselective Transformations of Terpenoids, Steroids, and Lipids in the Target-Oriented Synthesis of Low-Molecular-Weight Bioregulators,” state registry no. AAAA-A20-120012090023-8).

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    Yu. V. Myasoedova, E. R. Nurieva, L. R. Garifullina, N. M. Ishmuratova & G. Yu. Ishmuratov

Authors
  1. Yu. V. Myasoedova
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  2. E. R. Nurieva
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  3. L. R. Garifullina
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  4. N. M. Ishmuratova
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  5. G. Yu. Ishmuratov
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Correspondence to Yu. V. Myasoedova.

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The authors declare the absence of conflict of interest.

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Myasoedova, Y.V., Nurieva, E.R., Garifullina, L.R. et al. Transformations of Peroxide Products of Non-1-ene Ozonolysis by the Action of Carboxylic Acid Hydrazides. Russ J Org Chem 57, 113–116 (2021). https://doi.org/10.1134/S1070428021010164

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  • DOI: https://doi.org/10.1134/S1070428021010164

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