Abstract
Electrophilic and free radical additions to 5-ethylidenebicyclo[2.2.1]hept-2-ene and 5-vinylbicyclo-[2.2.1]hept-2-ene have been carried out with peracetic acid, hydrogen chloride, and methanol. In contrast to chlorosulfonyl isocyanate, peracetic acid primarily attacks the exocyclic double bond in 5-ethylidenebicyclo[2.2.1]hept-2-ene. Several other electrophilic additions are discussed which demonstrate the unpredictable reactivity of the norbornyl system.
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