There are two plausible reaction pathways; one is that anoxonium intermediate directly reacts with resorcinol, and theother is that an acyclic bisacetal, formed through thetransacetalization of a cyclic acetal with the solvent alcohols,reacts with resorcinol (Scheme 2). To determine the mainpathway of the macrocyclization reactions, 1,1,10,10-tetrakispropyloxydecane was subjected to the reaction in n-propanolinstead of 4c, which resulted in a significant reduction in theyield of 1c from 97% to 61% yield. Therefore, the oxonium ionof the cyclic acetal most likely reacts with resorcinol, and thetransacetalization process might be negligible. A cyclic acetal iscommonly in equilibrium with its open oxonium ion in acidicalcohols. At high temperatures, the equilibrium is pushedtoward the entropically favored open form, which canaccelerate the macrocyclization reaction. Accordingly, themacrocyclization requires high temperatures to obtain thebisresorcinarenes.
There are two plausible reaction pathways; one is that anoxonium intermediate directly reacts with resorcinol, and theother is that an acyclic bisacetal, formed through thetransacetalization of a cyclic acetal with the solvent alcohols,reacts with resorcinol (Scheme 2). To determine the mainpathway of the macrocyclization reactions, 1,1,10,10-tetrakispropyloxydecane was subjected to the reaction in n-propanolinstead of 4c, which resulted in a significant reduction in theyield of 1c from 97% to 61% yield. Therefore, the oxonium ionof the cyclic acetal most likely reacts with resorcinol, and thetransacetalization process might be negligible. A cyclic acetal iscommonly in equilibrium with its open oxonium ion in acidicalcohols. At high temperatures, the equilibrium is pushedtoward the entropically favored open form, which canaccelerate the macrocyclization reaction. Accordingly, themacrocyclization requires high temperatures to obtain thebisresorcinarenes.<br>
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