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Abstract:
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In 1967 Pedersen published the first of four fundamental papers on the synthesis and properties of macrocyclic polyether compounds. 1 "4 This class of compounds was discovered by accident during the preparation of bis-(<9-hydroxyphenoxy)ethyl ether (1) by reaction of bis chloroethyl) ether with the sodium salt of o-hydroxyphenoxytetrahydropyran followed by acid hydrolysis. Along with the anticipated product 1, Pedersen isolated a small quantity of a by-product. Investigation into the structure of the byproduct identified the compound as macrocyclic polyether 2 which was formed by the cyclic condensation of 2 moles of unprotected catechol, a small amount of which was present in the reactant, with 2 moles of bis(chloroethyl) ether. |