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Stereospecific hydrogenolysis of benzylic alcohols over Pd/C

  • Harvey, Freya M. Department of Chemistry, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, Switzerland
  • Bochet, Christian G. Department of Chemistry, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, Switzerland
    05.06.2020
Published in:
  • The Journal of Organic Chemistry. - 2020, vol. 85, no. 11, p. 7611–7619
English Hydrogenolysis of tertiary benzylic alcohols on palladium on carbon (Pd/C) generally proceeds with inversion of configuration. However, little is known about the hydrogenolysis mechanism of primary and secondary benzylic alcohols. Literature precedents suggest that these substrates may interact differently with the catalyst. To study the mechanism, we synthesized a pair of deuterated diastereoisomers with a chiral center at the benzylic position. Chemical derivatization of the hydrogenolysis products showed that the reaction proceeds with inversion of configuration for these substrates.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
License
License undefined
Identifiers
Persistent URL
https://folia.unifr.ch/unifr/documents/308679
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