ChemInform Abstract: Synthesis of Penta‐ and Hexacyclic Hydrocarbons by Hydrogenation of Binor‐S on Pt‐ and Ni‐Containing Heterogeneous Catalysts.

Abstract

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A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid

“…In this study, we developed a new method for the synthesis of pentacyclo[7.3.1.1 4,12 .0 2,7 .0 6,11 ]tetradecane (diamantane) 1 by skeletal hydroisomerization of endo-endo-heptacyclo [8.4.0.0 2,12 .0 3,8 .0 4,6 .0 5,9 .0 11,13 ]tetradecane (binor-S) 2 on treatment with sulfuric acid. When the reaction was ultrasonically assisted, the reaction time decreased to 2 h with the yield of diamantane 1 being retained (62%).…”

“…The reaction of hydrocarbon 2 with hydrochloric acid proceeds as the addition of HCl to the cyclopropane ring and results in the formation of a mixture of mono-and dichloro derivatives, the synthesis of which was reported in. [13,14] When sulfuric acid is replaced by an ionic liquid prepared from triethylamine and sulfuric acid, [15] the reaction follows a different route: binor-S 2 is converted to two isomeric hexacyclic hydrocarbons, hexacyclo[8.4.0.0 2,7 .0 3,14 .0 4,8 .0 9,13 ]tetradec-5-ene 4а…”

“…In particular, the most suitable initial compounds for the preparative synthesis of diamantane are three isomeric polycyclic hydrocarbons C14H20 3а-с, which are obtained by hydrogenation of norbornadiene dimer, heptacyclo[8.4.0.0 2,12 .0 3,8 .0 4,6 .0 5,9 .0 11,13 ]tetradecane (binor-S)…”

“…Binor-S is hydrogenated in the presence of a platinum catalyst (Н2PtCl6, PtO2) in glacial acetic acid under drastic conditions: 200°С and 305 atm of H2 [8,9]. In the presence of…”

A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid

“…In particular, the most suitable initial compounds for the preparation of diamantane are three isomeric polycyclic hydrocarbons C 14 H 20 3а – с , which are obtained by hydrogenation of the norbornadiene dimer, heptacyclo[8.4.0.0 2,12 .0 3,8 .0 4,6 .0 5,9 .0 11,13 ]tetradecane (binor-S, 2 ). Binor-S is hydrogenated in the presence of a platinum catalyst (Н 2 PtCl 6 , PtO 2 ) in glacial acetic acid under high pressure conditions at 70 °С and 200 psi of H 2 [ 8 – 9 ]. In the presence of superacid catalysts, such as B(OSO 2 CF 3 ) 3 , CF 3 SO 3 H/SbF 5 1:1, CF 3 SO 3 H/B(OSO 2 CF 3 ) 3 1:1 [ 10 ], NaBH 4 /CF 3 SO 3 H [ 11 ], or zeolite Y in the NaH form (NaY) [ 12 ], hydrocarbons 3a – c isomerize to diamantane in up to 99% yield ( Scheme 1 ).…”