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

2017-06-12T13:57:20Z (GMT) by Paul 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.