Synthesis and Properties of Bicyclohexa-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 back 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.
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