The reversible nature of the imine bond formation in CDCl(3) solution has been exploited to exchange substituted for unsubstituted m-phenylenediamine (MPD) units in hemicarcerand octaimines. Moreover, acid-catalyzed imine exchange has been shown to provide a novel mechanism whereby ferrocene (Fc) can be released as an entrapped guest from the hemicarceplex C(2)B(4)Fc dissolved in CDCl(3) to give the hemicarcerand C(2)B(4) when excess of both MPD and trifluoroacetic acid are present.
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Ro et al. (2000) studied this question.
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