Arylcyclopropylcarbinyl cations

The 2-aryl substituted cyclopropylcarbinyl cations have partial homoallylic character, whose contribution to the resonance hybrid increases when strong electron-withdrawing substituents (e.g. phenyl) are attached at the C2. Thus, 3-arylcyclobutyl tosylates on acetolysis give the homoallylic acetates predominantly, through the intermediate formation of the 2-arylcyclopropylcarbinyl cations (equation 21). 

In arylcyclopropylcarbinyl cations of the type 82 it was also found that the electron demand at the carbocation center, as determined by the aryl substituent X, also influenced the AJ values, which were correlated by the equation AJ = (1-h0.6[Pg.596]

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