Everything about Dewar Benzene totally explained
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Dewar benzene or
bicyclo[2.2.0]hexa-2,5-diene is the
bicyclic isomer of
benzene with the molecular formula C
6H
6. The compound is named after
James Dewar who, it's said, (incorrectly) proposed this structure for
benzene in 1867.
The compound itself was first synthesized in 1962 as a
tert-butyl derivative and then as the unsubstituted compound in 1963 by
photolysis of cis-1,2-dihydro derivative of
phthalic anhydride followed by
oxidation with
lead tetraacetate. Unlike benzene, Dewar benzene isn't flat; the two cyclobutene rings make an angle. The compound has nevertheless considerable
strain energy and reverts back to benzene with a
chemical half-life of two days. This thermal conversion is relatively slow because it's
symmetry forbidden based on orbital symmetry arguments.
With regards to Dewar's original claim, one study didn't find any evidence for this in the original article and only goes as far as to state that Dewar in it identified the structure as one of 7 possible isomers.
Other classic benzene isomers are
prismane,
benzvalene and
Claus benzene.
Further Information
Get more info on 'Dewar Benzene'.
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