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Reaction of Methylidenecycloalkanes with BF3·THF Catalyzed by Cp2TiCl2

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Abstract

The reaction of methylidenecycloalkanes with BF3·THF in the presence of Cp2TiCl2 as catalyst has been performed for the first time to obtain 1-fluoroboriranes spiro-fused to cycloalkanes and 1-methylcycloalk-1-enes formed as a result of isomerization of the initial olefin. The product structure was confirmed by one- (1H, 13C DEPT, 11B, 19F) and two-dimensional (COSY, HSQC, HMBC) NMR and mass spectra in combination with quantum chemical calculation of 13C chemical shifts.

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ACKNOWLEDGMENTS

The spectral studies were performed at the Agidel regional joint center, Ufa Federal Research Center, Russian Academy of Sciences.

Funding

This work was financially supported in the framework of state assignment no. FMRS-2022-0075.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 450075, Ufa, Russia

    L. I. Tulyabaeva, R. R. Salakhutdinov, A. R. Tulyabaev & T. V. Tyumkina

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

    M. F. Abdullin

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  1. L. I. Tulyabaeva
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  2. R. R. Salakhutdinov
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  3. A. R. Tulyabaev
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Correspondence to L. I. Tulyabaeva.

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Tulyabaeva, L.I., Salakhutdinov, R.R., Tulyabaev, A.R. et al. Reaction of Methylidenecycloalkanes with BF3·THF Catalyzed by Cp2TiCl2. Russ J Org Chem 58, 1976–1983 (2022). https://doi.org/10.1134/S1070428022120296

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