Abstract
(E)-2,2,5,5-Tetramethyl-3,4-diphenylhex-3-ene does not iodinate under normal conditions. Silver trifluoromethanesulfonate catalysis of the silver sulfate/iodine promoted reaction is shown to add versatility to this reation and successfully produce (E)-3-(4'-iodophenyl)-2,2,5,5-tetramethyl-4-phenylhex-3-ene and (E)-2,2,5,5-tetramethyl-3,4-di(4'-iodophenyl)hex-3-ene in good yield under mild conditions. Success is shown to be dependent upon the presence of a trace of water in the dichloromethane solvent.