K. Oyaizu, Hiroyuki Yonemaru, Tomokazu Iwasaki
Jan 4, 2003
Citations
0
Influential Citations
3
Citations
Journal
Journal of Macromolecular Science, Part A
Abstract
It has been established that the protonation of aryl sulfoxides under strongly acidic conditions produces hydroxysulfonium cations which readily react with suitable aromatic molecules, thus yielding aromatic sulfonium cations. This reaction has been exploited for the synthesis of poly(methylsulfonio-1,4-phenylenethio-1,4-phenylene triflate) from 4(methylsulfinyl)phenyl phenyl sulfide and triflic acid. The product can be converted to an engineering plastic poly(thio-1,4-phenylene) (PPS) by nucleophilic demethylation using pyridine. On the other hand, the superacidification of a more simple aryl sulfoxide compound, methylsulfinylbenzene, produces only the corresponding dimer, methyl{4-(methylsulfinyl)phenyl}(phenyl)sulfonium triflate; a further propagation reaction is impeded by the decrease in the electron density at the para position of the terminal phenyl ring due to the electron withdrawing effect of the sulfonio group. It has also been found that the admixture of methylsulfinylbenzene and triflic acid provides oligo(methylsulfonio-1,4-phenylene triflate) only when the reaction is carried out in