Abstract
Insoluble polymer-bound nucleophilic reagents were prepared by modification of crosslinked poly(4-vinylpyridine), poly(4-vinylpyridine-co-styrene) and poly(4-vinylpyridine-co-methyl methacrylate) with n-butyl bromide and subsequent reaction with the sodium salts of carboxylic acids and sodium-β-naphthoxide. These reagents were used for the preparation of carboxylic acid esters by their reactions with alkyl halide and alkylation of β-naphthoxide with benzyl chloride. The products were obtained in high yields and the polymer by-products could be regenerated and re-used with some loss of activity. The product distribution of C/O-alkylation of β-naphthoxide was found to be affected by the nature of the micro-environment.
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