| Abstract: | As an extension of earlier work on the condensation of ferrocene with aldehydes, the polycondensation of ferrocene with p- and o-carboxybenzaldehyde is described. While, in the former case, regular polycondensation occurs giving rise to a polymer composed of ferrocenylene and 4-carboxybenzal units, a deviation from this route is observed in the o-carboxybenzaldehyde case, where a polymer containing both carboxybenzal and 3,3-phthalide bridging units between the ferrocenylene groups is formed instead. This unexpected behavior can be accounted for by a hydride abstraction mechanism. In support of the polymer structure proposed, 3-ferrocenylphthalide and 3,3-diferrocenylphthalide are isolated as intermediates or by-products. In both polymer series, number-average molecular weights up to 3000 (unsubfractionated) are measured. The polymers are soluble in a number of organic solvents and can be cured with epoxides. |
