Anatomy of ene and Diels–Alder reactions between cyclohexadienes and azodicarboxylates
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 11,p. 1961-1964
- https://doi.org/10.1039/p29900001961
Abstract
In contrast with other (C ⋯ H ⋯ N) hydrogen transfers, the high-pressure kinetics of the ene reaction between cyclohexa-1,4-diene and diethyl azodicarboxylate show a concerted transition state. The discrepancy is assigned to the enhanced rigidity of the cyclohexadiene molecule with orthogonal hydrogen transfer to the nitrogen atom. Cyclohexa-1,3-diene reacts with diethyl azodicarboxylate according to a concerted Diels–Alder reaction.Keywords
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