Synthesis, Table of Contents 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, GermanyFax: +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 Recommend Article Abstract Buy Article All articles of this category 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 Full Text References 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 2 Gutsche CD. Calixarenes The Royal Society of Chemistry; Cambridge: 1992. 3 Gutsche CD. Calixarenes Revisited The Royal Society of Chemistry; Cambridge: 1998. 4 Calixarenes 2001 Asfari Z. Böhmer V. Harrowfield JM. Vicens J. Kluwer Academic Publishers; Dordrecht: 2001. 5 Calixarenes in Action Mandolini L. Imperial College Press; London: 2000. 6 Vicens J. Böhmer V. Calixarenes, A Versatile Class of Macrocyclic Compounds Kluwer Academic Press; Dordrecht: 1991. 7 Motta L. Regnouf-de-Vains J.-B. Bavoux C. Perrin M. J. Chem. Crystallogr. 1995, 25: 401 8 Motta-Viola L. Regnouf-de-Vains J.-B. Perrin M. Tetrahedron Lett. 2000, 41: 7023 9 Muthukrishnan R. Gutsche CD. J. Org. Chem. 1979, 44: 3962 10 Gutsche CD. Dhawan B. Leonis M. Stewart D. Org. Synth. Coll. 68: 238 ; Org. Synth. Coll. Vol. VIII, 1993, 77 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.
