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Synthesis 2006(13): 2097-2099  
DOI: 10.1055/s-2006-942410
PAPER
© Georg Thieme Verlag Stuttgart · New York

Concave Reagents. [1] Calix[6]arenes Bearing Camphorsulfonyl Substituents

Serge Konrada, Christian Nätherb, Ulrich Lüning*a
a Otto-Diels-Institut für Organische Chemie, Christian-Albrechts-Universität zu Kiel, Olshausenstr. 40, 24098 Kiel, Germany
Fax: +49(431)8801558; e-Mail: luening@oc.uni-kiel.de;
b Institut für Anorganische Chemie, Christian-Albrechts-Universität zu Kiel, Olshausenstr. 40, 24098 Kiel, Germany
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Publikationsverlauf

Received 3 April 2006
Publikationsdatum:
08. Juni 2006 (online)

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Abstract

The reaction of p-tert-butylcalix[6]arene with (+)-camphor-10-sulfonyl chloride gives either a mono-O-sulfonylated product or the fully O-sulfonylated calixarene. The crystal structure of mono-O-camphorsulfonylated p-tert-butylcalix[6]arene suggests that its sluggish reaction with further sulfonyl chloride can probably be explained by a conformation in which the narrow rim is covered by the camphor residue.

Key words

calixarenes - heterocycles - macrocycles - sulfonates - supram­olecular chemistry

    References

  • 1Part 49 of the series concave reagents. For part 48 see:
  • 1 Lüning U. Eggert J. P. W. Hegemann K. Eur. J. Org. Chem.  2006,  2747 
    CrossrefGoogle Scholar
  • 2 Gutsche CD. Calixarenes   The Royal Society of Chemistry; Cambridge: 1992. 
    Google Scholar
  • 3 Gutsche CD. Calixarenes Revisited   The Royal Society of Chemistry; Cambridge: 1998. 
    Google Scholar
  • 4 Calixarenes 2001   Asfari Z. Böhmer V. Harrowfield JM. Vicens J. Kluwer Academic Publishers; Dordrecht: 2001. 
    Google Scholar
  • 5 Calixarenes in Action   Mandolini L. Imperial College Press; London: 2000. 
    Google Scholar
  • 6 Vicens J. Böhmer V. Calixarenes, A Versatile Class of Macrocyclic Compounds   Kluwer Academic Press; Dordrecht: 1991. 
    Google Scholar
  • 7 Motta L. Regnouf-de-Vains J.-B. Bavoux C. Perrin M. J. Chem. Crystallogr.  1995,  25:  401 
    CrossrefGoogle Scholar
  • 8 Motta-Viola L. Regnouf-de-Vains J.-B. Perrin M. Tetrahedron Lett.  2000,  41:  7023 
    CrossrefGoogle Scholar
  • 9 Muthukrishnan R. Gutsche CD. J. Org. Chem.  1979,  44:  3962 
    CrossrefGoogle Scholar
  • 10 Gutsche CD. Dhawan B. Leonis M. Stewart D. Org. Synth. Coll.  68:  238 ; Org. Synth. Coll. Vol. VIII, 1993, 77
    Google Scholar
11

The relative orientation of neighboring aryl rings in calixarenes can be determined from the difference in chemical shift of the two doublets of the CH2 group. See ref. 2, p. 110ff.