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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzoquinones / chemistry*
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Crystallography, X-Ray
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Cyclooctanes / chemical synthesis*
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Cyclooctanes / chemistry
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Hydrocarbons / chemical synthesis*
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Hydrocarbons / chemistry
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Molecular Structure
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Polycyclic Aromatic Hydrocarbons / chemical synthesis*
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Polycyclic Aromatic Hydrocarbons / chemistry
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Polycyclic Compounds / chemical synthesis*
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Polycyclic Compounds / chemistry
Substances
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Benzoquinones
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Cyclooctanes
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Hydrocarbons
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Polycyclic Aromatic Hydrocarbons
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Polycyclic Compounds
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dibarrelane
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quinone