Aromatische[1,7]-sigmatropische H-Verschiebungen in o-(Buta-1,3-dienyl)-phenolen

Authors

  • R. Hug Organisch-Chemisches Institut der Universität Zürich
  • H.-J. Hansen Organisch-Chemisches Institut der Universität Zürich
  • H. Schmid Organisch-Chemisches Institut der Universität Zürich

DOI:

https://doi.org/10.2533/chimia.1969.108

Abstract

cis-o-(Penta-1,3-dienyl)-phenols (1 und 2) and their trans-isomers (3 and 4) on heating in octane at 121° and 190° respectively cyclise to 2-ethyl Δ3-chromene (5). cis-o- and trans-o-(Buta-1,3-dienyl)-phenols show the same behaviour and give 2-methyl Δ3-chromene. It is shown by deuterium labelling that the cyclisation of the phenols is induced by aromatic [1,7] and [1,5] sigmatropic H-shifts.

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Published

1969-03-31

Issue

Vol. 23 No. 3 (1969): Forschung/Research

Section

Kurze Mitteilungen

License

Copyright (c) 1969 R. Hug

Creative Commons License

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

How to Cite

[1]
R. Hug, H.-J. Hansen, H. Schmid, Chimia 1969, 23, 108, DOI: 10.2533/chimia.1969.108.