Pyrolysis of bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic anhydride

Abstract
The pyrolysis of the titled anhydride at low pressures and short contact times was found by both mass spectral and chemical experiments to involve an unusual decarboxylation to benzocyclobutenone. The latter subsequently decarbonylates to give a triad of C7H6 isomers: 5-vinylidenecyclopentadiene, ethynylcyclopentadiene, and benzocyclopropene. No evidence was found for dehydronorbornadiene, which would be expected on the basis of the pyrolysis of maleic anhydride or phthalic anhydride.

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