38589-62-7Relevant academic research and scientific papers
A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid
Aminov, Rishat I.,Khusnutdinov, Ravil I.
, p. 2534 - 2539 (2021/06/25)
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-endoheptacyclo[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-endopentacyclo[7.3.1.12,5.18,10.03,7]tetradecane in 68% yield with excellent selectivity (100%).
Synthesis and X-ray diffraction study of triamantane
Khusnutdinov, Ravil I.,Mukminov, Rinat R.,Aminov, Rishat I.,Khalilov, Leonard M.,Mescheryakova, Ekaterina S.,Dzhemilev, Usein M.
, p. 536 - 538 (2015/03/13)
Triamantane was synthesized in 80% yield by skeletal isomerization of a mixture of heptacyclo(8.8.0.02,17.03,11.04,9.012,16.013,18)octadecane and heptacyclo(8.8.0.02,13.03,11.04,9.012,17.014,18)octadecane under the action of the ionic liquid 2AlCl3-Et3N·HCl and mild conditions (50 °C, 8 h). X-ray diffraction analysis confirms the structure of the obtained product.
Synthesis of Triamantane
Hollowood, Fredric S.,McKervey, M. Anthony,Hamilton, Robert,Rooney, John J.
, p. 4954 - 4958 (2007/10/02)
Triamantane, the third member of the diamondoid hydrocarbon series, has been synthesized efficiently in five easy stages from norbornadiene.Acid-catalyzed rearrangement of the norbornadiene dimer, binor S (5), either in solution using silver perchlorate or in gas phase on silica gel, gives two hexacyclic olefins (13 and 14) suitable (without separation) for further elaboration: cycloaddition with butadiene gives C18 adducts whose hydrogenated forms (26 and 27) are converted by aluminum chloride catalyzed rearrangement into triamantane in 60percent yield.Byuse of isoprene instead of butadiene in the cycloaddition stage the synthesis can be modified to produce 9-methyltriamantane.The mechanism of the binor S rearrangement is discussed.
