An analytical evaluation of anhydrosugar polymerizations

Abstract 1,6‐Anhydro‐2,3,4‐tri‐ O ‐( p ‐methylbenzyl)‐β‐D‐glucopyranose (TXGL, M 1 ) has been copolymerized with 1,6‐anhydro‐2,3,4‐tri‐ O ‐benzyl‐β‐D‐glucopyranose (TBGL, M 2 ). Reactivity ratios, calculated by the Mayo and Lewis procedure, are r 1 = r 2 = 1.25 ± 0.25. Within experimental error these values represent azeotropic copolymerization. Therefore preceding interpretations of the relative reactivity of TXGL and other benzylated anhydrosugars are not incorrect because the possible effect of p ‐methyl substitution was ignored. Analysis of this copolymerization system and the reported copolymerizations of TXGL with 1,6‐anhydro‐2,3,4‐tri‐ O ‐benzyl‐β‐D‐manno‐(TBMN) and galactopyranoses (TBGA) by the linear method recently proposed by Kelen and Tudos has confirmed that true copolymerization takes place in all the systems mentioned above and that the classical copolymerization theory adequately describes the copolymerization mechanism. Physical properties of the copolymers of TXGL and TBGL indicate the usual high stereoregularity of structure.