Chirality induction in cyclocopolymerization. 13. Structural effect of 1,3-diol as chiral templates in the cyclocopolymerization of bis(4-vinylbenzoate)s with styrene

Two diastereomeric chiral cycloalkanediols such as (1S,2R)-2-hydroxymethyl- 1-cyclohexanol (a) and (1S,2S)-2-hydroxymethyl-1-cyclohexanol (bi, which we re conformational restriction models for (S)-1,3-butanediol (c), were used as chiral templates tu investigate the conformational effect uf the 1,3-dio l skeleton of the template moiety in the cyclocopolymerization of bis(4-vin ylbenzoate)s (1) with styrene. The specific rotation for the resulting temp late-free polymer 3a was almost twice that for 3b. In comparison with chira l template c, the efficiency of the chirality induction increases in the or der of b < c < a. These characteristics of chiral templates were discussed in terms of the conformational distribution of the monomer 1a-c.