Stereochemistry of congested cyclophanes containing chiral spirobiindanol phosphonates: Syntheses, X-ray structure, HPLC enantioresolution and clathration properties

European Journal of Organic Chemistry

Volumn , Issue 11, 1999, Pages 2799-2806

  Consiglio, Giuseppe A ^a   Finocchiaro, Paolo ^a   Failla, Salvatore ^b   Hardcastle, Kenneth I ^c   Ross, Candace ^c   Caccamese, Salvatore ^a   Giudice, Giuseppe ^a  

^a UNIVERSITY OF CATANIA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

Circular dichroism; Cyclophanes; Inclusion compounds; Phanes

Indexed keywords

MACROCYCLIC COMPOUND; PHOSPHONIC ACID DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; CHIRALITY; CONFORMATION; CRYSTAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SOLID STATE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 0032752516     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199911)1999:11<2799::aid-ejoc2799>3.0.co;2-%23     Document Type: Article

References (31)

1. [1a] Cyclophanes I. Topics in Current Chemistry (Ed.: F. Vögtle), Springer, Berlin, 1983; Vol. 113.
2. [1b] Cyclophanes II. Topics in Current Chemistry (Ed.: F. Vögtle); Springer, Berlin, 1983; Vol. 115.
3. [1c] Cyclophane Chemistry (Ed.: F. Vögtle), Wiley, Chichester 1993.
4. F. Diederich, Cyclophanes. Monographs in Supramolecular Chemistry (Ed.: J. F. Stoddart), The Royal Society of Chemistry, London 1991.
5. Comprehensive Supramolecular Chemistry (Eds.: D. D. MacNicol, F. Toda, R. Bishop); Pergamon, Oxford, 1996; Vol. 6.
6. [4a] J.-M. Lehn, Angew. Chem. Int. Ed. Engl. 1988, 27, 89-112.
7. [4b] D. J. Cram, Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020.
8. [4c] F. Diederich, Angew. Chem. Int. Ed. Engl. 1988, 27, 362-386.
9. [4d] A. Collet, Tetrahedron 1987, 43, 5725-5759.
10. [4e] K. Koga, K. J. Odashima, J. Incl. Phenom. 1989, 7, 53-60.
11. [4f] D. N. Reinhoudt, J. Jr. Herman, H. Den, Bull Soc. Chim. Belg. 1988, 97, 645-653.
12. [4g] D. N. Reinhoudt, P. Dijkstra, Pure Appl. Chem. 1988, 60, 477-482.
13. [5a] Weber, E. Progress in Macrocyclic Chemistry (Synthesis of Macrocycles, the Design of Selective Complexing Agents) (Eds.: R. M. Izatt, J. J. Christensen), John Wiley & Sons, New York, 1989; Vol. 3, pp. 337.
14. [5b] A. D. Hamilton, A. Muehldorf, S.-K. Chang, N. Pant, S. Goswami, D. van Engen, J. Incl. Phenom. 1989, 7, 27-38.
15. [5c] J. Jr. Rebek, Angew. Chem. Int. Ed. Engl. 1990, 29, 245-247.
16. [5d] S. C. Zimmerman, W. Wu, J. Am. Chem. Soc. 1989, 111, 8054-8055.
17. G. A. Consiglio, S. Failla, P. Finocchiaro, V. Siracusa, Phosphorus, Sulfur Silicon 1998, 134/135, 413-418.
18. B. Dhawan, D. Redmore, J. Org. Chem. 1984, 49, 4018-4021.
19. G. A. Consiglio, S. Failla, P. Finocchiaro, K. I. Hardcastle, M. Visi, Supramol. Chem. 1999.
20. K. Nakanishi, N. Berova, The Exciton Chirality Method, in Circular Dichroism: Principles and Applications (Eds.: K. Nakanishi, N. Berova, R. W. Woody), VCH Publishers, Inc., New York, 1994; pp. 361-398.
21. S. Hagishita, K. Kuriyama, M. Hayashi, Y. Nakano, K. Shigu, M. Nakagawa, Bull. Chem. Soc. Jpn. 1971, 44, 496-505.
22. R. J. Kazlauskas, J. Am. Chem. Soc. 1989, 111, 4953-4959.
23. C. R. Woods, M. Benaglia, F. Cozzi, J. S. Siegel, Angew. Chem. Int. Ed. Engl 1996, 35, 1830-1833.
24. S, Allenmark, Chromatographic Enantioseparation. Methods and Applications, Ellis Horwood, New York, 1991; p.51.
25. G. M. Sheldrick, Acta Crystallogr., 1990, A46, 467.
26. "SHELXTL/PC V5.0" Bruker Analytical X-Ray Instruments, Inc., Madison, WI, U.S.A.
27. G. M. Sheldrick, Program for Structure Refinement, University of Goettingen, Germany 1993.
28. International Tables for X-ray Crystallography (Ed.: A. J. C. Wilson), Vol. C. Kluwer Academic Publishers, Dordrecht: Tables 6.1.1.4 (pp. 500-502) and 4.2.6.8 (pp. 219-222), 1992.
29. C. K. Fair, "MolEN" Structure Determination System, Enraf-Nonius, Delft, The Netherlands 1990.
30. "XCAD4, Program for Processing CAD4 Diffractometer Data", K. Harms and S. Wocadlo, Bruker AXS, Inc., Madison, WI.
31. "XP/PC" Molecular Graphics Software, Bruker Analytical X-Ray Instruments, Inc., Madison, WI, USA.