Abstract Acetolysis of 4-(cyclopent-1'-enyl) butyl and 3-(2'-methylenecyclopentyl) propyl derivatives, but not 3-(cyclohex-1'-enyl) propyl and 2-(2'-methylenecyclohexyl) ethyl derivatives, occurs with π-bond participation (95 and 92%, respectively) to give similar, including maybe identical, cationic species involving the 8-hydrindyl cation. On the basis of product composition, the 8-hydrindyl cations when generated from spiro [4, 4] non-1-yl (σ- ...
