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 journalArticlepeer-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 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

ASJC Scopus subject areas

  • Organic Chemistry

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