Dynamic hemicarcerands and hemicarceplexes

S Ro; S J Rowan; A R Pease; D J Cram; J F Stoddart

doi:10.1021/ol005962p

Dynamic hemicarcerands and hemicarceplexes

Org Lett. 2000 Aug 10;2(16):2411-4. doi: 10.1021/ol005962p.

Authors

S Ro¹, S J Rowan, A R Pease, D J Cram, J F Stoddart

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095-1569, USA.

PMID: 10956509
DOI: 10.1021/ol005962p

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Ethers, Cyclic / chemical synthesis*
Ethers, Cyclic / chemistry
Imines / chemical synthesis*
Imines / chemistry
Models, Molecular
Molecular Conformation
Phenylenediamines / chemistry*
Structure-Activity Relationship
Thermodynamics

Substances

Ethers, Cyclic
Imines
Phenylenediamines
3-phenylenediamine