Abstract
A new method was developed for the direct synthesis of the second representative of the homologous series of diamond-like hydrocarbons, diamantane, in 65% yield by hydroisomerization of the norbornadiene dimer, endo-endo-heptacyclo[8.4.0.02,12.03,8.04,6.05,9.011,13]tetradecane (binor-S) on treatment with concentrated sulfuric acid (98%). In the presence of H2SO4 of lower concentration (75–80%), the reaction stops after the hydrogenation step giving endo-endo-pentacyclo[7.3.1.12,5.18,10.03,7]tetradecane in 68% yield with excellent selectivity (100%).
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5 articles.
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1. Hexacyclotetradecenes as polycyclic fused exo-norbornene monomers: synthesis of cyclic olefin copolymers via Ti-catalyzed controlled polymerization;Polymer Chemistry;2024
2. Synthesis of diamantane from new polycyclic hydrocarbons C14 under the action of ionic liquids;Mendeleev Communications;2023-07
3. Synthesis of diamantane by skeletal isomerization of pentacyclo[6.6.0.02,6.03,13.010,14]tetradecane induced by ionic liquids;Mendeleev Communications;2023-01
4. Synthesis of adamantane by ionic liquid-promoted isomerization of tricyclo[5.2.1.02,6]decane and H2SO4-mediated hydroisomerization of pentacyclo[4.4.0.02,4.03,7.08,10]decane;Russian Chemical Bulletin;2022-01
5. 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;Industrial & Engineering Chemistry Research;2021-08-23