Reaction of Nucleophiles with Bridgehead Carbocations Derived from 1-Bromobicyclooctanes and 1-Bromobicyclononanes

Article abstract of DOI:10.1021/jo00223a035

Both intramolecular and intermolecular reactions of bridgehead carbocations are described.The carbocations are best generated from the corresponding halide with silver triflate.The carbocations reacted effectively with allyltrimethylsilane, ethyl acetoacetate, benzene, and enol silyl ethers.Bridgehead radicals were also examined.