2,6,9-Trioxabicyclo[3.3.1]nona-3,7-dienes and 2,4,6,8-Tetraoxaadamantanes: Novel chiral spacer units in macrocyclic polyethers

Supramolecular Chemistry

Volumn 14, Issue 5, 2002, Pages 383-397

  Wallfisch, B C ^a   Egger, T ^a   Heilmayer, W ^a   Kappe, C O ^a   Wentrup, C ^b   Gloe, K ^c   Belaj, F ^a   Klintschar, G ^a   Kollenz, G ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b UNIVERSITY OF QUEENSLAND   (Australia)

^c DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Bridged bisdioxines; HPLC; Macrocyclic polyethers; Novel chiral spacer units; Tetraoxaadamantanes; X ray

Indexed keywords

2,4,6,8 TETRAOXAADAMANTANE; 2,6,9 TRIOXABICYCLO[3.3.1]NONA 3,7 DIENE; ACID; ADAMANTANE DERIVATIVE; ALKADIENE; BRIDGED COMPOUND; CHLORIDE; ESTER DERIVATIVE; ETHYLENE GLYCOL; METAL ION; POLYETHER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL PARAMETERS; CHEMICAL REACTION; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; POLYMERIZATION; TRANSESTERIFICATION; X RAY ANALYSIS;

EID: 0036022802     PISSN: 10610278     EISSN: None     Source Type: Journal    
DOI: 10.1080/1061027021000003430     Document Type: Article

References (45)

1. Kappe, C.O., Evans, R.A., Kennard, C.H.L. and Wentrup, C. (1991), J. Am. Chem. Soc. 113, 4234.
2. Kappe, C.O., Färber, G., Wentrup, C. and Kollenz, G. (1992), J. Org. Chem. 57, 7078.
3. Kappe, C.O., Färber, G., Wentrup, C. and Kollenz, G. (1992), Tetrahedron Lett. 33, 4553.
4. Kappe, C.O., Kollenz, G., Fabian, W.M.F., Wentrup, C. and Färber, G. (1993), J. Org. Chem. 58, 3361.
5. Heilmayer, W., Dalvi, T.S., Kappe, C.O., Wentrup, C., Gruber, K., Sterk, H. and Kollenz, G. (1995), J. Chem. Soc. Chem. Commun., 797.
6. Arnold, Z. and Budesinsky, M. (1988), J. Org. Chem. 53, 5352.
7. Voegtle, F., Haendel, M., Meier, S., Ottens-Hildebrandt, S., Ott, F. and Schmidt, T. (1995), Liebigs Ann. Chem., 739.
8. Wilson, R.S. and Tulchinsky, L. (1993), J. Org. Chem. 58, 1407.
9. Ottens-Hildebrandt, S., Meier, S., Schmidt, W. and Voegtle, F. (1994), Angew. Chem. 106, 1818.
10. Ottens-Hildebrandt, S., Meier, S., Schmidt, W. and Voegtle, F. (1994), Angew. Chem. Int. Ed. Engl. 33, 1767.
11. Sun, Y., Drovetskaya, T., Bolskar, R.D., Bau, R., Boyd, P.D.W. and Reed, C.A. (1997), J. Org. Chem. 62, 3642.
12. Ross, H. and Lüning, U. (1995), Angew. Chem. 107, 2723.
13. Ross, H. and Lüning, U. (1995), Angew. Chem. Int. Ed. Engl. 34, 2555.
14. Ranganathan, D., Haridas, V., Madhusudanan, K.P., Roy, R., Nagaraj, R. and John, G.B. (1997), J. Am. Chem. Soc. 119, 11578.
15. Izatt, R.M., Bradshaw, J.S., Nielson, S.A., Lamb, J.D. and Christensen, J. (1985), Chem. Rev. 85, 271.
16. Delangle, P., Dutasta, J.P., Declerq, J.P. and Tinant, B. (1998), Chem. Eur. J. 4, 100.
17. Bako, P., Vizvardi, K., Toppet, S., van Eycken, E., Hoornaert, G.J. and Toeke, L. (1998), Tetrahedron 54, 14975.
18. Campayo, L., Bueno, J.M., Navarro, P., Opchoa, C., Jimenez-Barbero, J., Pepe, G. and Samat, A. (1997), J. Org. Chem. 62, 2684.
19. Mlinaric-Majerski, K. and Kragol, G. (2001), Tetrahedron 57, 449.
20. Irrure, J., Riera, M. and Angel-Cintora, M. (2001), Synthesis, 647.
21. Faltin, F., Fehring, V., Kadyrov, R., Arrieta, A., Schareina, T., Selke, R. and Mietchen, R. (2001), Synthesis, 638.
22. Bradshaw, J.S., Baxter, S.L., Lamb, J.D., Izatt, R.M. and Christensen, J.J. (1981), J. Am. Chem. Soc. 103, 1821.
23. Ogawa, T., Yoshikawa, A., Wada, H., Ogawa, C., Ono, N. and Suzuki, H. (1995), J. Chem. Soc. Chem. Commun. 14, 1407.
24. Habata, Y., Fujishiro, F. and Akabori, S. (1996), J. Chem. Soc. Perkin Trans. 1, 953.
25. Knops, P., Sendhoff, N., Mekelburger, H.B. and Vögtle, F. (1991), Top. Curr. Chem. 161, 3.
26. Bax, A. and Summers, M.F. (1986), J. Am. Chem. Soc. 108, 2093.
27. Bax, A. and Subramanian, S. (1986), J. Magn. Res. 67, 565.
28. Lerner, H. and Bax, A. (1986), J. Magn. Res. 69, 375.
29. Podlaha, J., Podlahova, J., Arnold, Z., Maly, K. and Petricek, V. (1988), Acta Crystallogr. Sect. C 44, 1966.
30. Johnson, C.K. (1965) ORTEP. Report ORNL-3794 (Oak Ridge National Laboratory, Tennessee, USA).
31. Harwood, M.L. (1985), Aldrichim. Acta 18, 25.
32. Still, W.C., Kahn, M. and Mitra, M. (1978), J. Org. Chem. 43, 2923.
33. Hoss, A. and Voegtle, F. (1994), Angew. Chem. 106, 389.
34. Hoss, A. and Voegtle, F. (1994), Angew. Chem. Int. Ed. Engl. 33, 375.
35. Voegtle, F. and Jaeger, R. (1997), Angew. Chem. 109, 966.
36. Voegtle, F. and Jaeger, R. (1997), Angew. Chem. Int. Ed. Engl. 36, 930.
37. Fife, T.H. and Benjamin, B.M. (1973), J. Am. Chem. Soc. 95, 2059.
38. Fife, T.H. and Benjamin, B.M. (1974), J. Chem. Soc. Chem. Commun., 525.
39. Pollack, R.M. and Dumsha, T.C. (1975), J. Am. Chem. Soc. 97, 377.
40. Chiong, K.N.G., Lewis, S.D. and Shafer, J.A. (1975), J. Am. Chem. Soc. 97, 418.
41. Uray, G., Maier, N.M., Niederreiter, K.S. and Spitaler, M.M. (1998), J. Chromatogr. A 799, 67.
42. Gloe, K., Muehl, P. and Beger, J. (1988), Z. Chem. 28, 1.
43. Gloe, K. and Muehl, P. (1983), Isotopenpraxis 19, 257.
44. Sheldrick, G.M. (1997) SHELXS-97. Program for the Solution of Crystal Structures (University of Göttingen, Germany).
45. Sheldrick, G.M. (1997) SHELXL-97. Program for the Refinement of Crystal Structures (University of Göttingen, Germany).