Beilstein J. Org. Chem.2020,16, 2534–2539, doi:10.3762/bjoc.16.205
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%).
Keywords: binor-S; diamantane; hydroisomerization; sulfuric acid; tetrahydrobinor-S; Introduction
Among the highly diverse polycyclic and cage
the foregoing, we set ourselves the task to develop a one-pot method for the synthesis of diamantane (1) from binor-S (2).
Results and Discussion
In this study, we developed a new method for the synthesis of pentacyclo[7.3.1.14,12.02,7.06,11]tetradecane (diamantane, 1) by skeletal hydroisomerization
PDF
Graphical Abstract
Scheme 1:
Isomerization of 3а–с to diamantane (1). Reaction conditions: (a) CoBr2·2PPh3–BF3·OEt2, 110 °C, 12 ...