Chlorophenylsulfonyl phenoxide

Perhaps the first indication of chain-growth polymerization was realized in the synthesis of poly(phenylene sulfide) using p-halothiophenol salts. For certain monomers, it was realized that the pol5mier chain end groups were more reactive than the monomers. Later, in the polycondensation of chlorophenylsulfonyl phenoxide, an increased reactivity of the polymer end group was detected. The reaction scheme is shown in Figure 7.2. The polymeric end group reacts ca. 20 times faster than the monomer. 

Chloro-p-phenylenediamine, 431 Chlorophenylsulfonyl phenoxide, 245 Chlorophthalic anhydride, 476 Chlorophyll, 49... 

Scheme 2 Polymerization of metal p-halothiophenoxides Scheme 3 Polymerization of chlorophenylsulfonyl phenoxide...

In the condensation polymerization of chlorophenylsulfonyl phenoxide, increased reactivity of the polymer end group was demonstrated by the relation between conversion and reaction time (Scheme 3). Furthermore, comparison of the rate constants for the displacement of chlorine atoms with hydroxide showed that a model of the polymer end group reacted 20 times faster than the monomer. Thus, the electronic effects of a substituent in one ring were transmitted to the other via the sulfone linkage [5]. 

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