Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon

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

doi:10.1021/jo5003455

Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon

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

Waseda University

Research output: Contribution to journal › Article

3 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 C_2v symmetry.

Original language	English
Pages (from-to)	2803-2808
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	79
Issue number	6
DOIs	https://doi.org/10.1021/jo5003455
Publication status	Published - 2014 Mar 21

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo5003455

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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

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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.",

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AU - Shimizu, Isao

AU - Kobayashi, Susumu

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