Abstract
This paper describes the selective synthesis of multifunctional, linear unsaturated oligomers of p-hydroxy-, p-acetoxy-, and p-hydroxy-m-methoxy-styrenes (p-HOSt, p-AcOSt, and p-HO-m-MeOSt, respectively). A linear unsaturated dimer of p-AcOSt was selectively formed by oxo acids or their derivatives (CF3SO3H or AcClO4) in benzene at 70°C. p-AcOSt trimer and tetramer were also produced in high yields by the proper choice of catalysts and reaction conditions. Base-catalyzed hydrolysis of the p-AcOSt dimer and trimer quantitatively gave the corresponding p-HOSt oligomers not obtainable by direct reactions by p-HOSt itself. This finding provides a new method for preparing multifunctional phenols with linear unsaturated backbone, which are attractive as “reactive oligomers.” p-HO-m-MeOSt, whose oligomers are structurally related to lignin, was also converted to a linear unsaturated dimer in good yield by iodine or CH3SO3H catalyst.
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Higashimura, T., Hiza, M. Cationic Oligomerization of p-Hydroxystyrenes: Selective Preparation of Linear Styrene Dimers with Functional Groups. Polym J 13, 563–568 (1981). https://doi.org/10.1295/polymj.13.563
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DOI: https://doi.org/10.1295/polymj.13.563