Dynamic hemicarcerands and hemicarceplexes.
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)&crcldt;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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Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095-1569, USA.
Rowan
S J
SJ
Pease
A R
AR
Cram
D J
DJ
Stoddart
J F
JF
D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D010655:Phenylenediamines / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013816:Thermodynamics
D004988:Ethers, Cyclic; D007097:Imines; D010655:Phenylenediamines; C008381:3-phenylenediamine