Preparation of p-phenylene-3,3′-bis(1-allyltetrahydrothiophenium) dibromide and its reactions in basic solution

Abstract

p-Phenylene-3,3′-bis(1-allyltetrahydrothiophenium) dibromide 1, prepared from p-phenylene-3,3′-diacrylaldehyde 3, when treated with aqueous sodium hydroxide gave a sulfonium salt polymer. Pyrolysis of this in an attempt to form the highly conjugated polymer, poly(p-phenylenehexa-1,3,5trienylene) gave, however, only carbonyl-containing compounds. Although no polymerization occurred in basic methanol, a reaction intermediate was shown by UV–VIS and ¹H NMR spectroscopy to have been formed.