Collect. Czech. Chem. Commun.
2004, 69, 1345-1361
https://doi.org/10.1135/cccc20041345
Doubly Bridged Calix[8]crowns
Corrada Geracia,*, Grazia M. L. Consolia, Mario Piattellia and Placido Nerib,*
a Istituto di Chimica Biomolecolare, Sezione di Catania, C.N.R., Via del Santuario 110, I-95028 Valverde (CT), Italy
b Dipartimento di Chimica, Università di Salerno, Via S. Allende, I-84081 Baronissi (SA), Italy
References
1a. C., Dradi E., Pochini A., Ungaro R., Andreetti G. D.: J. Chem. Soc., Chem. Commun. 1983, 1075.
<https://doi.org/10.1039/c39830001075>
1b. Z., Wenger S., Vicens J.: J. Inclusion Phenom. Mol. Recogn. Chem. 1994, 19, 137, and references therein.
<https://doi.org/10.1007/BF00708979>
1c. Casnati A., Ungaro R., Asfari Z., Vicens J. in: Calixarenes 2001 (Z. Asfari, V. Böhmer, J. Harrowfield and J. Vicens, Eds), p. 365. Kluwer, Dordrecht 2001.
2a. Vicens J., Böhmer V. (Eds): Calixarenes, a Versatile Class of Macrocyclic Compounds. Kluwer, Dordrecht 1991.
2b. V.: Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
<https://doi.org/10.1002/anie.199507131>
2c. A., Shinkai S.: Chem. Rev. 1997, 97, 1713.
<https://doi.org/10.1021/cr960385x>
2d. Gutsche C. D.: Calixarenes Revisited. The Royal Society of Chemistry, Cambridge 1998.
2e. Asfari Z., Böhmer V., Harrowfield J., Vicens J. (Eds): Calixarenes 2001. Kluwer, Dordrecht 2001.
3a. C. J.: Angew. Chem., Int. Ed. Engl. 1988, 27, 1021.
<https://doi.org/10.1002/anie.198810211>
3b. Gokel G.: Crown Ethers and Cryptands. Royal Society of Chemistry, Cambridge 1991.
3c. Dietrich B., Viout P., Lehn J.-M.: Macrocyclic Chemistry, Aspects of Organic and Inorganic Supramolecular Chemistry. VCH, Weinheim 1993.
4a. R., Casnati A., Ugozzoli F., Pochini A., Dozol J.-F., Hill C., Rouquette H.: Angew. Chem., Int. Ed. Engl. 1994, 33, 1506.
<https://doi.org/10.1002/anie.199415061>
4b. Z., Harrowfield J. M., Sobolev A. N., Vicens J.: Aust. J. Chem. 1994, 47, 757.
<https://doi.org/10.1071/CH9940757>
4c. H., Shinkai S.: Chem. Lett. 1994, 1115.
<https://doi.org/10.1246/cl.1994.1115>
4d. A., Pochini A., Ungaro R., Bocchi C., Ugozzoli F., Egberink R. J. M., Struijk H., Lugtenberg R., de Jong F., Reinhoudt D. N.: Chem. Eur. J. 1996, 2, 436.
<https://doi.org/10.1002/chem.19960020413>
4e. R. A., Urvoas A., Bryan J. C., Haverlock T. J., Hay B. P., Moyer B. A.: Chem. Commun. 1999, 1751.
<https://doi.org/10.1039/a905682c>
4f. V., Dozol J. F., Fuangswasdi S., Arnaud-Neu F., Thuery P., Nierlich M., Asfari Z., Vicens J.: J. Chem. Soc., Perkin Trans. 2 1999, 271.
<https://doi.org/10.1039/a806714g>
4g. Z., Thuery P., Nierlich M., Vicens J.: Tetrahedron Lett. 1999, 40, 499.
<https://doi.org/10.1016/S0040-4039(98)02421-6>
4h. Z., Thuery P., Nierlich M., Vicens J.: Aust. J. Chem. 1999, 52, 343.
<https://doi.org/10.1071/CH98167>
5a. A., Pochini A., Secchi A.: Eur. J. Org. Chem. 2000, 2325.
<https://doi.org/10.1002/1099-0690(200006)2000:12<2325::AID-EJOC2325>3.0.CO;2-E>
5b. H. F., Dabestani R., Brown G. M., Sachleben R. A.: Chem. Commun. 2000, 833.
<https://doi.org/10.1039/a908720f>
5c. H., Gloe K., Paulus E. F., Saadioui M., Böhmer V.: Org. Lett. 2000, 2, 839.
<https://doi.org/10.1021/ol005581b>
5d. A. P., Chong H.-S., Pavan K. T., Huang Z., Alihodzic S., Watson W. H., Ejsmont K.: Tetrahedron 2002, 58, 10205.
<https://doi.org/10.1016/S0040-4020(02)01360-1>
5e. S. K., Sim W., Vicens J., Kim J. S.: Tetrahedron Lett. 2003, 44, 805.
<https://doi.org/10.1016/S0040-4039(02)02657-6>
5f. S. K., Vicens J., Park K.-M., Lee S. S., Kim J. S.: Tetrahedron Lett. 2003, 44, 993.
<https://doi.org/10.1016/S0040-4039(02)02721-1>
5g. V., Grün A., Bitter I.: Tetrahedron Lett. 2003, 44, 4681.
<https://doi.org/10.1016/S0040-4039(03)01077-3>
6a. D., Arnecke R., Böhmer V., Vogt W.: Tetrahedron 1993, 49, 6019.
<https://doi.org/10.1016/S0040-4020(01)87186-6>
6b. J. L. M., Böhmer V., Vogt W.: Tetrahedron Lett. 1995, 36, 2445.
<https://doi.org/10.1016/0040-4039(95)00277-J>
6c. R., Mandolini L., Arnecke R., Böhmer V., Vogt W.: J. Chem. Soc., Perkin Trans. 2 1998, 419.
<https://doi.org/10.1039/a703966b>
6d. S., Notti A., Pappalardo S., Parisi M. F., Principato G.: Tetrahedron 1999, 55, 5505.
<https://doi.org/10.1016/S0040-4020(99)00195-7>
6e. S., Notti A., Pappalardo S., Parisi M. F., Principato G.: J. Inclusion Phenom. Mol. Recogn. Chem. 2000, 36, 67.
<https://doi.org/10.1023/A:1008062428030>
7a. A., Jacopozzi P., Pochini A., Ugozzoli F., Cacciapaglia R., Mandolini L., Ungaro R.: Tetrahedron 1995, 51, 591.
<https://doi.org/10.1016/0040-4020(94)00918-K>
7b. J. S., Chen Y. Y., Lu X. R.: Tetrahedron 1999, 55, 10365.
<https://doi.org/10.1016/S0040-4020(99)00578-5>
7c. Y. Y., Li J. S., Xin J., Zhong Z. L., Gong S. L., Lu X. R.: Synth. Commun. 1999, 29, 705.
<https://doi.org/10.1080/00397919908085820>
7d. Y. Y., Yang F. F., Lu X. R.: Tetrahedron Lett. 2000, 41, 1571.
<https://doi.org/10.1016/S0040-4039(99)02332-1>
7e. Y. Y., Yang F. F., Gong S. L.: Tetrahedron Lett. 2000, 41, 4815.
<https://doi.org/10.1016/S0040-4039(00)00729-2>
7f. Y. Y., Yang F. F.: Chem. Lett. 2000, 484.
<https://doi.org/10.1246/cl.2000.484>
7g. M. T., Farmer D. B., Brodbelt J. S., Goolsby B. J.: J. Am. Chem. Soc. 2000, 122, 1486.
<https://doi.org/10.1021/ja991810h>
7h. Y., Yang F., Thuery P., Nierlich M., Vicens J.: J. Inclusion Phenom. Mol. Recogn. Chem. 2002, 42, 261.
<https://doi.org/10.1023/A:1016088905683>
8. Neri P., Geraci C., Piattelli M. in: Recent Research Developments in Organic Chemistry (S. G. Pandalai, Ed.), Vol. 1, p. 285. Transworld Research Network, Trivandrum 1997.
9a. C., Piattelli M., Neri P.: Tetrahedron Lett. 1996, 37, 3899.
<https://doi.org/10.1016/0040-4039(96)00684-3>
9b. F., Chen Y.: Eur. J. Org. Chem. 2001, 365.
<https://doi.org/10.1002/1099-0690(200101)2001:2<365::AID-EJOC365>3.0.CO;2-N>
10a. C., Piattelli M., Neri P.: Tetrahedron Lett. 1995, 36, 5429.
<https://doi.org/10.1016/0040-4039(95)00997-Q>
10b. C., Chessari G., Piattelli M., Neri P.: Chem. Commun. 1997, 921.
<https://doi.org/10.1039/a701114h>
11. C., Piattelli M., Chessari G., Neri P.: J. Org. Chem. 2000, 65, 5143.
<https://doi.org/10.1021/jo0002036>
12. C., Piattelli M., Neri P.: Tetrahedron Lett. 1996, 37, 7627.
<https://doi.org/10.1016/0040-4039(96)01678-4>
13. For a discussion on chemical shift of OH groups in partially alkylated calix[8]arenes, see ref. 11 and F., Consoli G. M. L., Piattelli M., Neri P.: J. Org. Chem. 1998, 63, 6852.
<https://doi.org/10.1021/jo9805091>
14. For examples of the use of OH chemical shift as a structural probe, see refs 6a, 13 and P., Battocolo E., Cunsolo F., Geraci C., Piattelli M.: J. Org. Chem. 1994, 59, 3880.
<https://doi.org/10.1021/jo00093a020>
15. Molecular modeling was performed with MacroModel V4.5 computer program: F., Richards N. G. J., Guida W. C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W. C.: J. Comput. Chem. 1990, 11, 440.
<https://doi.org/10.1002/jcc.540110405>
16a. J. O., de Mendoza J., Pons M.: J. Org. Chem. 1997, 62, 4518.
<https://doi.org/10.1021/jo961943a>
16b. S., Bottino A., Cunsolo F., Parlato S., Neri P.: Tetrahedron: Asymmetry 2000, 11, 3103.
<https://doi.org/10.1016/S0957-4166(00)00273-1>
17. S., Principato G., Geraci C., Neri P.: Tetrahedron: Asymmetry 1997, 8, 1169.
<https://doi.org/10.1016/S0957-4166(97)00115-8>
18a. A., Suzuki Y., Shinkai S.: Tetrahedron: Asymmetry 1998, 9, 97.
<https://doi.org/10.1016/S0957-4166(97)00611-3>
18b. C., Bottino A., Piattelli M., Gavuzzo E., Neri P.: J. Chem. Soc., Perkin Trans. 2 2000, 185.
<https://doi.org/10.1039/a909410e>
19. K. A., Fronczek F. R., Watson W. H., Kashyap R. P., Gutsche C. D.: J. Org. Chem. 1991, 56, 7256.
<https://doi.org/10.1021/jo00026a015>
20a. C.: J. Fed. Proc. Fed. Am. Soc. Expl. Biol. 1968, 27, 1305.
20b. A., Pochini A., Reverberi S., Ungaro R., Andreetti G. D., Ugozzoli F.: Tetrahedron 1986, 42, 2089.
<https://doi.org/10.1016/S0040-4020(01)87626-2>
21. S., Hogen Esch T. E., Smid J.: Macromolecules 1973, 6, 133.
<https://doi.org/10.1021/ma60031a021>
22. A., Pochini A., Ungaro R., Ugozzoli F., Arnaud F., Fanni S., Schwing M.-J., Egberink R. J. M., de Jong F., Reinhoudt D. N.: J. Am. Chem. Soc. 1995, 117, 2767.
<https://doi.org/10.1021/ja00115a012>
23a. F., Asfari Z., Souley B., Vicens J.: New J. Chem. 1996, 20, 453.
23b. Z., Lamare V., Dozol J. F., Vicens J.: Tetrahedron Lett. 1999, 40, 691.
<https://doi.org/10.1016/S0040-4039(98)02422-8>
24. J. H., Gutsche C. D.: Org. Synth. 1990, 68, 243.

