Abstract
A doubly-crowned calix and a double-calixcrown derived from 4,6,10,12,16,18,22,24,25,26,27, 28-dodecamethyl-5,11,17, 23-tetrahydroxycalix[4]arene (1) have been prepared by reaction of appropriate oligoethylene glycol ditosylates with (1) in acetonitrile in the presence of potassium carbonate. A potassium template effect is observed during one of the double cyclizations.
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References and Notes
C. D. Gutsche: inCalixarenes, Monographs in Supramolecular Chemistry, J. F. Stoddart (Ed.), The Royal Society of Chemistry, Cambridge, 1989.
J. Vicens and V. Böhmer: inCalixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers, Dordrecht, 1991.
R. Ungaro and A. Pochini: inFrontiers in Supramolecular Organic Chemistry and Photochemistry, J. Schneider and H. Dürr (Eds.), VCH Verlagsgesellsschaft, Weinheim, 1991.
E. Ghidini, F. Ugozzoli, R. Ungaro, S. Harkema, A. A. El-Fold, and D. N. Reinhoudt:J. Am. Chem. Soc. 112, 6979 (1990).
Z. Asfari, R. Abidi, F. Arnaud, and J. Vicens:J. Incl. Phenom. 13, 163 (1992).
The name of themesitol derived calix[4]arene (1) according to Ref. 1: 4,6,10,12,16,18,22,24, 25,26,27,28-dodecamethyl-5,11,17, 23-tetrahydroxycalix[4]arene.
S. Pappalardo, F. Bottino, and G. Ronsisvalle:Phosphorus Sulfur,19, 327 (1984).
Z. Asfari, S. Pappalardo, F. Baert, and J. Vicens: unpublished work.
A typical procedure is described for the preparation of (7): a slurry ofmesitol derived calix[4jarene (1) (1.18 g, 2 mmol), pentaethylene glycol ditosylate (2.20 g, 4 mmol), and potassium carbonate (3.75 g, 6 mmol), and acetonitrile (300 mL) was refluxed under nitrogen for 24 h. The solvent was evaporated to dryness under reduced pressure. The residue was taken up in chloroform and washed with 5% HCl. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated. The residue was precipitated with ethanol to afford pure doubly-crowned calix[4]arene (7) (1.15 g, 58%).Characterisation data for (5)1H-NMR (CDCl3, with CHCl3 at 7.26 ppm): 3.94–3.49 (m, 32 H, OCH2CH2O and aromatic-CH2-aromatic), 2.32 (s, 24H, ext. CH3), and 1.14 (s, 12 H, int. CH3); FAB positionm/z = 820.4.Elemental analysis calc. for C52H6808·C2H5OH: C% 74.79 H% 8.60.Found C% 74.61 H% 8.25. For (6)1H-NMR: 3.88–3.66 (m, 40 H, OCH2CH2O and aromatic-CH2-aromatic), 2.32 (s, 24 H, ext. CH3), and 1.09 (s, 12 H, int. CH3); FAB positivem/z = 908.5.Elemental analysis calc. for C56H76O10·C2H5OH: C% 72.58 H% 8.76.Found C% 72.12 H% 8.37. For (7)1H-NMR: 3.89–3.48 (m, 48 H, OCH2CH2O and aromatic-CH2-aromatic), 2.32 (s, 24 H, ext·CH), and 1.09 (s, 12 H, int. CH); FAB positivem/z = 996.4.Elemental analysis calc. for C60H84O12·C2H5OH: C% 71.37 H% 8.69.Found C% 71.52 H% 8.56. For (9)1H-NMR: 6.87 (s, 8 H, aromatics in the glycol chain), 4.25–3.77 (m, 40 H, OCH2CH0 and aromatic-CH2-aromatic), 2.32 (s, 24 H, ext. CH3), and 1.12 (s, 12 H, int. CH3); FAB positivem/z = 1092.5.Elemental analysis calc. for C68H84O12: C% 74.69 H% 7.74.Found C% 74.39 H% 7.58. For (10)1H-NMR: 6.73 (s, 16 H, aromatics in the glycol chain), 4.04–3.38 (m, 80 H, OCH2CH2O and aromatic-CH2-aromatic), 2.27 (s, 24 H, ext. CH3), 2.10 (s, 24 H, int. CH3), and 0.912 (s, 24 H, int. CH3); FAB positivem/z =2184.0.Elemental analysis calc. for C136H168O24: C% 74.69 H% 7.74.Found C% 74.57 H% 7.71.
J. F. Stoddart:Chem. Brit. 714 (1991).
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Asfari, Z., Pappalardo, S. & Vicens, J. New preorganized calix[4]arenes. Part I. A doubly-crowned calix and a double-calixcrown derived from 4,6,10,12,16,18,22,24,25,26,27,28-Dodecamethyl-5,11,17,23-tetrahydroxycalix[4] arene. J Incl Phenom Macrocycl Chem 14, 189–192 (1992). https://doi.org/10.1007/BF01029667
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DOI: https://doi.org/10.1007/BF01029667