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

Rishat Aminov; Ravil Khusnutdinov

doi:10.3762/bxiv.2021.24.v1

Synthesis of polycyclic hydrocarbons C₁₄H₂₀ by hydrogenation of exo-exo-, exo-endo-, endo-exo-, and endo-endo- hexacyclo[9.2.1.0^2,10.0^3,8.0^4,6.0^5,9]tetradec-12-enes with H₂SO₄ and isomerization of the products to diamantane induced by ionic liquids

Rishat Aminov and
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

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Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Abstract

A new method was developed for hydrogenation of unsaturated hexacyclic norbornadiene dimers, exo-exo-, exo-endo-, endo-exo-, and endo-endo- hexacyclo[9.2.1.0^2,10.0^3,8.0^4,6.0^5,9]tetradec-12-enes, using sulfuric acid (98%), giving pentacyclo[8.2.1.1^5,8.0^2,9.0^3,7]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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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)