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Title: The room-temperature stabilization of bicyclo[2.2.2]oct-1-ene and bicyclo[3.2.1]oct-1-ene
Authors: Roach, Paul
Warmuth, Ralf
Keywords: Carbenes
Hemicarcerands
Host–guest systems
Ring expansion
Strained molecules
Issue Date: 2003
Publisher: © Wiley-VCH
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.
Abstract: 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.
Version: Published
DOI: 10.1002/anie.200351120
URI: https://dspace.lboro.ac.uk/2134/25357
Publisher Link: http://dx.doi.org/10.1002/anie.200351120
ISSN: 1433-7851
Appears in Collections:Closed Access (Chemistry)

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