Rearrangement of the Diels–Alder adduct of azodibenzoyl and cyclopentadiene
- 1 January 1970
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 48 (1) , 81-88
- https://doi.org/10.1139/v70-013
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.Keywords
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