Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon

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

Research output: Contribution to journalArticle

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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Hydrocarbons
X ray crystallography
dibarrelane
octane

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

Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon. / Suzuki, Takahiro; Okuyama, Hiroshi; Takano, Atsuhiro; Suzuki, Shinya; Shimizu, Isao; Kobayashi, Susumu.

In: Journal of Organic Chemistry, Vol. 79, No. 6, 21.03.2014, p. 2803-2808.

Research output: Contribution to journalArticle

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, vol. 79, no. 6, pp. 2803-2808. https://doi.org/10.1021/jo5003455
Suzuki T, Okuyama H, Takano A, Suzuki S, Shimizu I, Kobayashi S. Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon. Journal of Organic Chemistry. 2014 Mar 21;79(6):2803-2808. https://doi.org/10.1021/jo5003455
Suzuki, Takahiro ; Okuyama, Hiroshi ; Takano, Atsuhiro ; Suzuki, Shinya ; Shimizu, Isao ; Kobayashi, Susumu. / Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon. In: Journal of Organic Chemistry. 2014 ; Vol. 79, No. 6. pp. 2803-2808.
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