Synthesis of polycyclic hydrocarbons C14H20 by hydrogenation of exo-exo-, exo-endo-, endo-exo-, and endo-endo- hexacyclo[9.2.1.02,10.03,8.04,6.05,9]tetradec-12-enes with H2SO4 and isomerization of the products to diamantane induced by ionic liquids
Submitting author affiliation: Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Ufa, Russian Federation
Beilstein Arch. 2021, 202124. https://doi.org/10.3762/bxiv.2021.24.v1
Published 18 Mar 2021
This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.
Abstract
A new method was developed for hydrogenation of unsaturated hexacyclic norbornadiene dimers, exo-exo-, exo-endo-, endo-exo-, and endo-endo- hexacyclo[9.2.1.02,10.03,8.04,6.05,9]tetradec-12-enes, using sulfuric acid (98%), giving pentacyclo[8.2.1.15,8.02,9.03,7]tetradecanes, which were subjected to skeletal rearrangement under the action of ionic liquids to form diamantane in up to 84% yield.
Keywords: diamantane; hexacyclic norbornadiene dimers, isomerization, ionic liquids, sulfuric acid
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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:
Aminov, R.; Khusnutdinov, R. Beilstein Arch. 2021, 202124. doi:10.3762/bxiv.2021.24.v1
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