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Monatshefte für Chemie / Chemical Monthly

, Volume 112, Issue 5, pp 679–682 | Cite as

Zur Regioselektivität einigerLewis-Säuren bei der katalysiertenDiels-Alder-Reaktion von Cyclopentadien mit Mesityloxid

Synthesen in der Isocamphanreihe, 16. Mitt. Kurze Mitteilung
  • Johann Bachner
  • Ulrike Huber
  • Gerhard Buchbauer
Organische Chemie und Biochemie

Zusammenfassung

The regioselectivity of 9Lewis acids in the catalyzedDiels-Alder-reaction of cyclopentadiene and mesityloxide is described and theendo: exo-ratio of1 a and1 b determined by quantitative HPLC- and1H-NMR-measurements. The reaction mixture of1 a+1 b normally contains more of theendo epimer1 a, e.g. 3∶1 for1 a∶1 b, and is therefore in agreement with theendo rule, only TiCl4 favors theexo epimer1 b.

Synthesis in the isocamphane series, XVI. The regioselectivity of some lewis acids in the catalyzed Diels-Alder-reaction of cyclopentadiene and mesityloxide

Short communication

Keywords

Diels-Alder reaction Endo:exo ratio Endo rule Lewis acids Regioselectivity 

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Copyright information

© Springer-Verlag 1981

Authors and Affiliations

  • Johann Bachner
    • 1
  • Ulrike Huber
    • 1
  • Gerhard Buchbauer
    • 1
  1. 1.Institut für Pharmazeutische ChemieUniversität WienWienÖsterreich

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