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Dewar benzene : ウィキペディア英語版
Dewar benzene

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Dewar benzene or bicyclo()hexa-2,5-diene is a bicyclic isomer of benzene with the molecular formula C6H6. The compound is named after James Dewar who included this structure in a list of possible C6H6 structures in 1867.〔

However, he did not propose it as the structure of benzene, and in fact he supported the correct structure previously proposed by August Kekulé in 1865.〔
==Synthesis and properties of bicyclo()hexa-2,5-diene==
The compound itself was first synthesized in 1962 as a ''tert''-butyl derivative
〕 and then as the unsubstituted compound by E.E. van Tamelen in 1963 by photolysis of ''cis''-1,2-dihydro derivative of phthalic anhydride followed by oxidation with lead tetraacetate.〔

:
Unlike benzene, Dewar benzene is not flat; the two cyclobutene rings make an angle. The compound has nevertheless considerable strain energy and reverts to benzene with a chemical half-life of two days. This thermal conversion is relatively slow because it is symmetry forbidden based on orbital symmetry arguments.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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