By A. Gandini, H. Cheradame

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As we shall see, this situation is in fact much more general than commonly believed, and ester formation is quite important with practically all Br6nsted acids. The composite anions derived from Lewis acids possess intrinsically the potential of undergoing a neutralisation reaction with the carbocation: ! CH 2 ~ + I + MtXn+ 1 I ) ~CH2-CX + MtXn. I The importance of this displacement reaction will depend upon the relative electrophilicity of the Lewis acid and the carbenium ion. Given the possible sources of neutralisation of the anions just discussed, it is surprising that almost no attempt has ever been made at following the fate of these species during a cationic polymerisation, except by measurements of electrical conductivity, which are however non-specific and incapable of detecting ion pairs.

30 II. Fundamentals Table 7. Rate constants for the reaction of benzyl and diphenylmethyl cations with various olefins in 1,2-dichloroethane at room temperature. Experimental uncertainty < _+20%. 7 × 107 concerning the reactivity of bare carbenium ions towards water and other strong nucleophfles 1t 3). Wang and Dorfman ~14) have recently measured the rate constants for the reaction of benzflium and diphenylmethylium ions with various olefins in ethylene chloride at room temperature. Some of these values are reported in Table 7.

The use of labelled molecules to clarify a reaction mechanism has often been applied to initiation of cationic polymerisation. The most successful results have been obtained by Russell et al. in the context of water cocatalysis in the polymerisation of isobutene by stannic chloride. Saegusa et al. have recently developed a method for killing a cationic polymerisation with phenoxide ions in order to "count" the number of active chains present in certain systems 1s 1). Cheradame et al. 93) have looked into the formation of titanium tetrachlorideindene addition products to prove the occurence of direct initiation.

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