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Study of the Features of the Reaction of Arylcyclopropanes with Nitrozonium Ethyl Sulfate or Nitrozonium Tetrafluoroborate

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Abstract

The reactions of diaryl-, aryl-, and alkyl–arylcyclopropanes with ethyl nitrite in the presence of sulfur trioxide and sulfur trioxide dioxane complex, as well as the reactions of 1-alkyl-2-arylcyclopropanes with NOBF4 were studied. It was found that the attack of the nitrosonium cation, accompanied by the formation of a benzyl carbocation, leads to the formation of isoxazolines. The introduction of bulky alkyl substituents into the cyclopropane ring changes the regioselectivity of nitrosation, favoring the attack of the electrophilic particle on the benzyl position and leading to the competitive formation of an alkyl carbocation. Depending on the structure of the alkyl substituent, both products of intramolecular heterocyclization accompanied by skeletal rearrangements and products formed with the participation of an external nucleophile are formed.

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ACKNOWLEDGMENTS

The authors are grateful to Thermo Fisher Scientific, MS Analytics (Moscow) and personally to Prof. A.A. Makarov for providing the mass spectrometric equipment used in this work.

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Authors and Affiliations

  1. Lomonosov Moscow State University, 119991, Moscow, Russia

    A. Yu. Gavrilova, O. B. Bondarenko, V. N. Tikhanushkina, T. A. Solodovnikova & N. V. Zyk

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  1. A. Yu. Gavrilova
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  2. O. B. Bondarenko
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  3. V. N. Tikhanushkina
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  4. T. A. Solodovnikova
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  5. N. V. Zyk
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Correspondence to A. Yu. Gavrilova.

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Gavrilova, A.Y., Bondarenko, O.B., Tikhanushkina, V.N. et al. Study of the Features of the Reaction of Arylcyclopropanes with Nitrozonium Ethyl Sulfate or Nitrozonium Tetrafluoroborate. Russ J Org Chem 56, 753–762 (2020). https://doi.org/10.1134/S107042802005005X

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