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

Paul Roach, Ralf Warmuth

Research output: Contribution to journalArticlepeer-review

47 Scopus citations


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 (see picture). 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.

Original languageEnglish (US)
Pages (from-to)3039-3042
Number of pages4
JournalAngewandte Chemie - International Edition
Issue number26
StatePublished - Jul 7 2003

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)


  • Carbenes
  • Hemicarcerands
  • Host-guest systems
  • Ring expansion
  • Strained molecules


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