Abstract
Abstract The electrophilic addition reactions of norbornadiene-fused furans, pyrroles, and thiophenes with bromine, arenesulfenyl chlorides, or a triazoledione generally afforded skeletally rearranged adducts except for a dibenzoyl-substituted thiophene. The formations of the adducts are attributable to the neighboring group participation by five-membered heteroaromatic rings, accompanied by the formations of bridged heteroarenium ions and the subsequent Wagner–Meewein type skeletal rearrangement.
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