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The room-temperature stabilization of bicyclo[2.2.2]oct-1-ene and bicyclo[3.2.1]oct-1-ene

journal contribution
posted on 2017-06-12, 13:57 authored by Paul RoachPaul Roach, Ralf Warmuth
Retardation through incarceration: The highly strained anti-Bredt bridgehead olefin bicyclo[2.2.2]oct-1-ene (1) is remarkably stable at 60 °C, if generated photochemically inside the hemicarcerand 2. The surrounding host not only prevents the dimerization of 1, but also retards strongly its intramolecular retro-Diels–Alder reaction by several orders of magnitude.

History

School

  • Science

Department

  • Chemistry

Published in

Angewandte Chemie International Edition

Volume

42

Issue

26

Pages

3039 - 3042

Citation

ROACH, P. and WARMUTH, R., 2003. The room-temperature stabilization of bicyclo[2.2.2]oct-1-ene and bicyclo[3.2.1]oct-1-ene. Angewandte Chemie (international edition), 42 (26), pp.3039-3042.

Publisher

© Wiley-VCH

Version

  • VoR (Version of Record)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2003

DOI

ISSN

1433-7851

eISSN

1521-3773

Publisher version

Language

  • en

Administrator link

Usage metrics

    Loughborough Publications

    Categories

    Keywords

    CarbenesHemicarcerandsHost–guest systemsRing expansionStrained moleculesChemical Sciences not elsewhere classified

    Licence

    CC BY-NC-ND 4.0

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