Abstract
Glycidyl esters, frequently employed as reactive groups on polymeric supports, were functionalized with alcohols as stoichiometric reagents, yielding β-alkoxyalcohols. Among the solvents studied, best results were obtained in ethers in the presence of a strong proton acid as a catalyst. Alcohols include simple alkanols, diols, protected polyols, 3-butyn-1-ol 3-hydroxypropanenitrile and cholesterol. This protocol represents a convenient way for introduction of various functionalities onto epoxy-functionalized polymers. Under the reaction conditions, some side reactions take place, mostly due to the reactive ester group and water present in the reaction mixture.
Highlights
Epoxides or oxiranes are among the most important groups of compounds in the field of organic synthesis.They are easy to prepare by a variety of synthetic methods, in most cases directly or indirectly from alkenes.Ring strain, polarity of C–O bond and basicity of oxygen atom make them substantially reactive and suitable intermediates for transformation to other classes of compounds.[1,2,3,4] The most extensively employed reaction of epoxides is a nucleophilic attack to one of ring carbons, accompanied by ring opening
Glycidyl methacrylate was replaced by glycidyl 4-chlorobenzoate, because of the simplicity of its preparation, easier tracking of the reaction by the glycidyl ester completely reacted (TLC) and simpler chromatographic separation of the products
A corresponding reaction of glycidyl esters is less straightforward, since the substrate contains an ester group, which is prone to react under the conditions of the ring opening addition
Summary
Epoxides or oxiranes are among the most important groups of compounds in the field of organic synthesis. Addition of oxygen nucleophiles to epoxides is limited to water and alcohols and, to a lesser extent, phenols and carboxylic acids. Hydroxy group of these compounds is a weak nucleophile and acid catalysis is generally required. Our background interest was functionalization of epoxy groups on solid polymer surface of crosslinked poly(glycidyl methacrylate) with alcohols, with the emphasis on long chain diols and (protected) polyols. We wished to avoid as much as possible the application of transition metal catalysts, since on insoluble polymers, functionalized with polar groups, a strong chelation of metal ions might occur and complete removal of the metal after the reaction can be difficult if not impossible. The results of reactions of a series of alcohols with a model epoxide, glycidyl 4-chlorobenzoate (1) in various solvents using different catalysts is presented
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