The reaction of 1,3-bisbromomethyl-2-methoxy benzene with diaza-15-crown-5 or diaza-18-crown-6 in acetonitrile gives the phenolic cryptands 6a and 6c; it is shown that the formation of 6a involves the methoxy cryptand salt 9 which undergoes efficient demethylation by bromide anion as a result of acid catalysis within the cavity of the cryptand system.
A. F. Sholl and I. O. Sutherland, J. Chem. Soc., Chem. Commun., 1992, 1252 DOI: 10.1039/C39920001252
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