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Alcoholysis of Binor-S with Alcohols under the Action of Ionic Liquid

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Abstract

Inorganic ionic liquids are first shown to catalyze the alcoholysis of heptacyclo-[8.4.0.02,12.03,8.04,6.05,9.011,13]tetradecane (heptacyclic dimer of norbornadiene, binor-S) with primary and secondary alcohols. The reaction occurs at 65−100°C for 6−14 h via regioselective cleavage of the cyclopropane C4−C5 bond in binor-S to form 10-exo-alkoxyhexacyclo[9.2.1.02,7.03,5.04,8.09,13] tetradecanes in 85−90% yields.

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Acknowledgments

Structural studies were performed using the equipment of the Agidel Regional Center for Collective Use.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, pr. Oktyabrya 141, Ufa, Republic of Bashkortostan, 4500075, Russia

    R. I. Aminov & R. I. Khusnutdinov

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  1. R. I. Aminov
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  2. R. I. Khusnutdinov
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Correspondence to R. I. Aminov.

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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 5, pp. 677–682.

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Aminov, R.I., Khusnutdinov, R.I. Alcoholysis of Binor-S with Alcohols under the Action of Ionic Liquid. Russ J Org Chem 55, 587–591 (2019). https://doi.org/10.1134/S1070428019050014

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  • DOI: https://doi.org/10.1134/S1070428019050014

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