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 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 hydrogenation step giving endo-endo-pentacyclo[184.108.40.206,5.18,10]tetradecane in 68% yield.
Keywords: diamantane, binor-S, tetrahydrobinor-S, hydroisomerization, sulfuric acid
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Aminov, R.; Khusnutdinov, R. I. Beilstein Arch. 2020, 202085. doi:10.3762/bxiv.2020.85.v1
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