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Synthesis of adamantane by ionic liquid-promoted isomerization of tricyclo[5.2.1.02,6]decane and H2SO4-mediated hydroisomerization of pentacyclo[4.4.0.02,4.03,7.08,10]decane

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Abstract

Adamantane was synthesized by skeletal isomerization of endo- and exo-tricyclo[5.2.1.02,6]-decanes in the presence of ionic liquid [Et3NH]+[Al2Cl7]−—CuSO4. A new method to synthesize adamantane in 75% yield by H2SO4-mediated hydroisomerization of its new precursor, pentacyclo[4.4.0.02,4.03,7.08,10]decane, was developed.

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Centre of the Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russia

    R. I. Aminov, I. R. Ramazanov & R. I. Khusnutdinov

Authors
  1. R. I. Aminov
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  2. I. R. Ramazanov
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  3. R. I. Khusnutdinov
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Corresponding author

Correspondence to I. R. Ramazanov.

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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 102–106, January, 2022.

This work was financially supported by the Russian Science Foundation (Project No. 19-73-20128). Adamantane-substituted substrates were synthesized in the framework of the State Task of the Ministry of Science and High Education of the Russian Federation (Project No. AAAA-A19-119022290009-3/FMRS-2022-0076). Structures of the synthesized compounds were evaluated using the equipment of the Regional Center for Collective Use of Unique Equipment “Agidel” at the Institute of Petrochemistry and Catalysis, UFRC RAS in the framework of the State Task (Project No. AAAA-A19-119022290004-8).

No human or animal subjects were used in this research.

The authors declare no competing interests.

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Aminov, R.I., Ramazanov, I.R. & Khusnutdinov, R.I. Synthesis of adamantane by ionic liquid-promoted isomerization of tricyclo[5.2.1.02,6]decane and H2SO4-mediated hydroisomerization of pentacyclo[4.4.0.02,4.03,7.08,10]decane. Russ Chem Bull 71, 102–106 (2022). https://doi.org/10.1007/s11172-022-3382-9

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  • DOI: https://doi.org/10.1007/s11172-022-3382-9

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