Bildung eines Azacyclols durch transanulare Ringkontraktion

Authors

  • Marlise Schläpfer-Dähler Organisch-chemisches Institut Universität Zürich Winterthurerstrasse 190, CH-8057 Zürich
  • Roland Prewo Organisch-chemisches Institut Universität Zürich Winterthurerstrasse 190, CH-8057 Zürich
  • Jost H. Bieri Organisch-chemisches Institut Universität Zürich Winterthurerstrasse 190, CH-8057 Zürich
  • Gabriel Germain Unité de Chimie Physique Moléculaire et Cristallographie, Université Catholique de Louvain, Bâtiment Lavoisier, B-1348 Louvain-la-Neuve.
  • Heinz Heimgartner Organisch-chemisches Institut Universität Zürich Winterthurerstrasse 190, CH-8057 Zürich

DOI:

https://doi.org/10.2533/chimia.1988.25

Abstract

Reaction of 3-dimethylamino-2,2-dimethyl-2H-azirine (1) with phthalimide (8) in polar solvents yields the (1:1)-adduct 2-dimethylamino-9b-hydroxy-3,3-dimethyl-5,9b-dihydro-3H-imidazo[2,1-a]isoindol-5-one (10). The structure of this azacyclol has been established by X-ray crystallography. A reaction mechanism via ring expansion to an eight-membered heterocycle followed by transannular ring contraction explains the formation of 10.

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Published

1988-01-31

Issue

Vol. 42 No. 1 (1988): Forschung/Research

Section

Articles

License

Copyright (c) 1988 Marlise Schläpfer-Dähler

Creative Commons License

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

How to Cite

[1]
M. Schläpfer-Dähler, R. Prewo, J. H. Bieri, G. Germain, H. Heimgartner, Chimia 1988, 42, 25, DOI: 10.2533/chimia.1988.25.