Facile Shifts of Bromine Atom on C-3 Position of Guaiazulene and Synthesis of Variously Functionalized Azulenes Using These Reactions

Article abstract of DOI:10.1246/cl.1989.353

Treatment of guaiazulene (1) with NBS in hexane gave exclusively 3-bromo compound, while in benzene it afforded various side-chain-brominated compounds.Shifts of bromine atom catalyzed by succinimide were observed in benzene, presumably via intermolecular radical pathways.Using these reactions, various side-chain-functionalyzed derivatives of 1, including epoxy compounds, were prepared.