Stereospecific and Unspecific Pathways for Aromatization of 1,4-Cyclohexadienes

Authors

  • Paul Müller Département de Chimie Organique Université de Genève 30, quai Ernest-Ansermet, CH-1211 Genève 4
  • Nicole Pautex Département de Chimie Organique Université de Genève 30, quai Ernest-Ansermet, CH-1211 Genève 4
  • Hans Hagemann Département de Chimie Physique, Université de Genève 30, quai Ernest-Ansermet, CH-1211 Genève 4

DOI:

https://doi.org/10.2533/chimia.1988.414

Abstract

The aromatization of trans-3,6-dideuterio-1,4-cyclohexadiene (1-d2) to benzene (2) with chromic acid is slightly stereospecific with a diastereomeric excess of 25%. This result is ascribed to two competing mechanisms, a stereospecific 2-electron oxidation with CrVI, and a non-specific 1-electron oxidation with CrlV. In contrast, aromatization of 1-d2 with lead tetraacetate exhibits no stereospecificity.

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Published

1988-12-31

Issue

Vol. 42 No. 12 (1988): Forschung/Research

Section

Articles

License

Copyright (c) 1988 Paul Müller

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
P. Müller, N. Pautex, H. Hagemann, Chimia 1988, 42, 414, DOI: 10.2533/chimia.1988.414.