Abstract
The product of the thermal isomerization of the Diels–Alder adduct 1 of azodibenzoyl and cyclopentadiene has been identified by degradation and nuclear magnetic resonance analysis as the cis-bicyclic oxadiazine 2a, the dihydro derivative of which has been synthesized. The isomerization is quantitative and is first order throughout in solution in a range of solvents ; kinetic and other evidence point to it being a sigmatropic rearrangement.
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