Beilstein J. Org. Chem.2022,18, 1424–1434, doi:10.3762/bjoc.18.148
equilibrium to the adamantane form by forming a stable boronate adduct 18 having a diamantane structure through the reaction with phenylboronic acid. Note that product 18 contains an unprecedented 2,4-dioxa-1,5,7,10-tetraaza-3-boraadamantane motif (Scheme 4). This result demonstrates that N-amino-substituted
supramolecular receptors. In particular, we have shown that the 1N,2O-TAAD derivative reacts with phenylboronic acid producing a novel type of boron ate-complex with a rigid diamantane geometry. 3N-TAADs bearing N-acyl and alkoxycarbonyl groups form guest–host complexes with water or methanol, in which the guest
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Graphical Abstract
Figure 1:
Adamantane-based tripodal scaffolds and current work.
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
diamondoid homologous series, which is produced on an industrial scale (prepared by AlBr3 or AlCl3-induced skeletal isomerization of a petrochemical monomer, hydrogenated dicyclopentadiene) [1], have been studied rather extensively, the chemical behavior of diamantane, the second member of the diamandoid
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Graphical Abstract
Scheme 1:
Isomerization of 3а–с to diamantane (1). Reaction conditions: (a) CoBr2·2PPh3–BF3·OEt2, 110 °C, 12 ...