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Synlett 1990; 1990(4): 186-190
DOI: 10.1055/s-1990-21028
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Substituent and Solvent Effects in Intramolecular Diets-Alder Reactions

Michael E. Jung*
  • *Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90024, USA
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Publication Date:
08 March 2002 (online)

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The development of our research concerning the substituent and solvent effects in intramolecular Diels-Alder reactions is presented. From this work we have determined the importance of relative factors in accelerating cyclizations due to the gem-dialkyl effect, established the enthalpic basis for this acceleration, and observed an important, heretofore unrecognized, solvent effect on intramolecular Diels-Alder reactions in which the diene and dienophile are attached by an ester linkage. 1. Introduction 2. The Basis for the gem-Dialkyl Effect: The Reactive-Rotamer Effect or the Thorpe-lngold Effect? 3. Solvent Effects in the Intramolecular Diels-Alder Reaction of Substrates Having an Ester Linkage 4. Conclusion

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