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

  1. Rishat AminovORCID Logo and
  2. Ravil Khusnutdinov

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

  • Preprint

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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Aminov, R.; Khusnutdinov, R. Beilstein Arch. 2021, 202124. doi:10.3762/bxiv.2021.24.v1

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