The 1,2-Alternate Conformation of Calix[4]arenes: A Rare Conformation? Dynamic 1H NMR Studies of Flexible Tetraalkylated Calix[4]arenes

Journal of the American Chemical Society

Volumn 113, Issue 7, 1991, Pages 2385-2392

  Groenen, Leo C ^a   van Loon, Jan Dirk ^a   Verboom, Willem ^a   Reinhoudt, David N ^a   Harkema, Sybolt ^a   Casnati, Alessandro ^b   Ungaro, Rocco ^b   Pochini, Andrea ^b   Ugozzoll, Franco ^c  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b UNIVERSITY OF PARMA   (Italy)

^c CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000065213     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00007a006     Document Type: Article

References (34)

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3. van Loon, J.-D.; Arduini, A.; Coppi, L.; Verboom, W.; Pochini, A.; Ungaro, R.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1990, 55, 5639–5646.
4. In this paper we use a schematic drawing of callx[4]arene in the form of a parallelogram, of which the corners represent the methylene bridges. Only the relative orientations of the alkoxy groups are shown for clarity, since the para substituents are always ie β-butyl groups.
5. Ghidini, E.; Ugozzoll, F.; Ungaro, R.; Harkema, S.; El-Fadl, A. A.; Reinhoudt, D. N. J. Am. Chem. Soc. 1990, 112, 6979–6985.
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19. Until now an adequate nomenclature for the exact conformation of a calix[4]arene is missing. In this paper we use the prefix syn to indicate that two large O-substituents (that cannot rotate through the annulus at room temperature) are on the same face of the molecule and the prefix anti when two large O-substituents are on different faces of the molecule. The numbers 1–4 indicate the four phenyl rings of the calix[4]arene in sequential order.
20. In tetrahydrofuran/dimethylformamide with sodium hydride as a base a 1:2 mixture of cone and partial cone was obtained.
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22. The anti-1,2-diethyl ether 7c was a quite unexpected product, that was found in a general study on the synthesis of monoalkylated calix[4]arenes starting from the corresponding tetraalkylated compounds. Casnatl, A.; Arduini, A.; Ghidini, E.; Pochini, A.; Ungaro, R. Tetrahedron, in press.
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25. These calculations were performed with the corrected VDW parameters for hydrogen atoms, as was suggested in a Newsletter from Polygen Corp., 1990.
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27. The procedure reported in ref 12b was slightly modified by using benzyl bromide instead of benzyl tosylate as the alkylating agent.
28. The procedure reported in ref 4 was slightly modified by using ethyl iodide instead of ethyl tosylate. This reduced the reaction time from 20 h to 5h.
29. Marion, D.; Wüthrich, K. Biochem. Biophys. Res. Commun. 1983, 113, 967–974.
30. Structure Determination Package, Frenz, B. A. and Associates Inc., College Station, TX, and Enraf Nonius, Delft, 1983.
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32. Sheldrick, G. M. shelx; Computer Programs for Crystal Structure Determinations, University of Cambridge, UK, 1980.
33. International Tables for X-ray Crystallography, Kynoch Press: Birmingham, England, 1974; Vol. IV, pp 72–98.
34. quanta 2.1 a, released August 1989, purchased from Polygen Corp., Waltham, MA.