Lithium Perchlorate as a Reagent for Synthesis of Covalently Bonded Organic Perchlorates via Electrophilic Additions of Halogens and Nitronium Tetrafluoroborate to Olefins

Article abstract of DOI:10.1021/jo00140a018

The reaction of a series of olefins with chlorine and bromine in the presence of a large excess of lithium perchlorate in ether gave 1,2-halo perchlorates together with the corresponding 1,2-dihalides.Analogous reactions of NO2BF4 in methylene chloride or ethyl acetate with monoolefins gave 1,2-nitro perchlorates.Norbornadiene reacted with a NO2BF4/LiClO4 system to give two isomeric nitro perchlorates of nortricyclenic structure.Several synthetic and mechanistic aspects of this new reaction of electrophilic perchloration of olefins are discussed.