PDF herunterladen
Synlett 1990; 1990(4): 186-190
DOI: 10.1055/s-1990-21028
account
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
08. März 2002 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

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