Chemistry of the Highly Strained Alkene Perfluorobicyclo[2.2.0]hex‐1(4)‐ene.

Several varieties of cycloaddition as well as nucleophilic and free radical addition to the highly reactive central bond of the title fluorocarbon (1) are described. [2 + 2] Cycloaddition to 1 has made available four of the five known representatives of the [2.2.2]propellane ring system, which are rare because of their extreme strain (in the absence of fluorine substitution) and high reactivity. Two of these, a propellanone and a propellene, are first reported here. Quantum mechanical calculations have shed light on many of these transformations. [ABSTRACT FROM AUTHOR]