Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon

Takahiro Suzuki, Hiroshi Okuyama, Atsuhiro Takano, Shinya Suzuki, Isao Shimizu, Susumu Kobayashi

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2 Citations (Scopus)

Abstract

The synthesis of a novel hydrocarbon, dibarrelane, has been accomplished in 11 steps via an intramolecular REDDA reaction of a masked o-benzoquinone, followed by Clemmensen reduction and Barton decarboxylation. The twisted structure of the tetracyclic dibarrelane skeleton was also clarified via X-ray crystallography. Finally, it was proposed that dibarrelane has C2 symmetry rather than C2v symmetry.

Original languageEnglish
Pages (from-to)2803-2808
Number of pages6
JournalJournal of Organic Chemistry
Volume79
Issue number6
DOIs
Publication statusPublished - 2014 Mar 21

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Suzuki, T., Okuyama, H., Takano, A., Suzuki, S., Shimizu, I., & Kobayashi, S. (2014). Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon. Journal of Organic Chemistry, 79(6), 2803-2808. https://doi.org/10.1021/jo5003455