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

^*Corresponding author for this work

Waseda University

Research output: Contribution to journal › Article › peer-review

4 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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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.",

author = "Takahiro Suzuki and Hiroshi Okuyama and Atsuhiro Takano and Shinya Suzuki and Isao Shimizu and Susumu Kobayashi",

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AU - Suzuki, Takahiro

AU - Okuyama, Hiroshi

AU - Takano, Atsuhiro

AU - Suzuki, Shinya

AU - Shimizu, Isao

AU - Kobayashi, Susumu

PY - 2014/3/21

Y1 - 2014/3/21

N2 - 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.

AB - 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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Synthesis of dibarrelane, a dibicyclo[2.2.2]octane hydrocarbon

Abstract

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