[3.3.2]- and [3.3.3]Propellanes in Reactions with Oxidizing Electrophiles
The structure of [3.3.2]- and [3.3.3]propellanes, their framework analogs, and their radical-cations was investigated by computational methods (BLYP and B3LYP) in the 6-31G* basis set. The reactivity of the propellanes toward model oxidizing electrophiles does not contradict the quantum-chemical calculations. In the case of the tetracyclic framework analog of [3.3.3]propellane the reaction takes place as C—H substitution, whereas in the case of [3.3.2]propellanes it takes place as C—C-oxidative addition.
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