Thermische und säurekatalysierte Umlagerung von N-(α,α-Dimethylallyl)-anilinen

Authors

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

DOI:

https://doi.org/10.2533/chimia.1976.21

Abstract

The thermal (t-amyl alcohol, 200 to 250°) and acid catalyzed (2N H2SO4, 50 to 70°) rearrangement of N-(α,α-dimethylallyl)- anilines 1 to yield the corresponding 2-(γ,γ-dimethylallyl)-anilines 2 is described. The kinetic secondary H/D isotope effect for the thermal (kH/kD = 0,83, 237°) as well as for the acid catalyzed (kH/kD  = 0,84, 67,5°) rearrangement of N-(α,α-dimethylallyl)- aniline (1a) and its β,γ,γ-d3 derivative is in agreement with a [3,3]-sigmatropic process in the neutral and charged species, respectively.

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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, 21, DOI: 10.2533/chimia.1976.21.