Thermische und säurekatalysierte Umlagerung o-substituierter N-(α-Methylallyl)-aniline

Authors

  • S. Jolidon Institut de Chimie Organique, Fribourg
  • H.-J. Hansen Institut de Chimie Organique, Fribourg

DOI:

https://doi.org/10.2533/chimia.1976.23

Abstract

The thermal (t-amyl alcohol, 290 to 310°) and acid catalyzed (2N H2SO4, 105 to 125°) rearrangement of 2-R-N-(α-methylallyl)- anilines 1 (R = H, CH3, t-C4H9) to yield (E)/(Z) mixtures of the corresponding 2-(but-2'-enyl)-6-R-anilines 2 is described. A strong dependence of the (E)/(Z) ratio with respect to the bulkiness of R is observed (see table). The fact that the ratio increases with the bulkiness of R is in accord with a preferred chair-like transition state in both types of aromatic amino-Claisen rearrangements.

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Published

1976-01-31

Issue

Vol. 30 No. 1 (1976): Forschung/Research

Section

Kurze Mitteilungen

License

Copyright (c) 1976 S. Jolidon

Creative Commons License

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

How to Cite

[1]
S. Jolidon, H.-J. Hansen, Chimia 1976, 30, 23, DOI: 10.2533/chimia.1976.23.