Allylic rearrangements of cyclo-octatetraenylmethanols

Abstract

Three alcohols in which the hydroxy-group is allylic to one of the double bonds of a cyclo-octatetraene ring have been prepared by condensation of cyclo-octatetraenyl-lithium with benzaldehyde and acraldehyde, and by reduction of the ketone obtained from cyclo-octatetraenyl-lithium and crotononitrile. In acid solution all three alcohols undergo allylic rearrangements, but only in the case of the alcohol derived from benzaldehyde is the major product formed by migration of the cyclo-octatetraene double bond.