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The reversible nature of the imine bond formation in CDCl3 solution has bee
n exploited to exchange substituted for unsubstituted m-phenylenediamine (M
PD) units in hemicarcerand octaimines. Moreover, acid-catalyzed imine excha
nge 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)circle dot
Fc dissolved in CDCl3 to give the hemicarcerand C2B4 when excess of both M
PD and trifluoroacetic acid are present.