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
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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.
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