Synthesis of chiral resorcinarene-based hosts and a mass spectrometric study of their chemistry in solution and the gas phase

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 56, Issue 3-4, 2006, Pages 381-394

  Beyeh, Ngong K ^a   Fehér, Domonkos ^b,c   Luostarinen, Minna ^a   Schalley, Christoph A ^b   Rissanen, Kari ^a  

^a UNIVERSITY OF JYVÄSKYLÄ   (Finland)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

^c UNIVERSITY OF HAWAII   (United States)

Author keywords

Chirality; Electrospray Mass Spectrometry; Gas phase chemistry; Host guest chemistry; Resorcinarenes

Indexed keywords

EID: 33846461384     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-006-9121-2     Document Type: Article

References (53)

1. M. Tunstad, A. Tucker, E. Dalcanale, J. Weiser, A. Bryant, C. Sherman, C. Helgeson, B. Knobler, and J. Cram: J. Org. Chem. 54, 1305 (1989).
2. P. Timmerman, W. Verboom, and D.N. Reinhoudt: Tetrahedron 52, 2663 (1996).
3. J.W. Steed and J.L. Atwood: Supramolecular Chemistry, Wiley, Chichester (2000).
4. A. Shivanyuk, M. Saadioui, F. Broda, I. Thondorf, M.O. Vysotsky, K. Rissanen, E. Kolehmainen, and V. Böhmer: Chem. Eur. J. 10, 2138 (2004).
5. D. Cram, S. Karbach, E. Kim, B. Knobler, F. Maverick, L. Ericson, and C. Helgeson: J. Am. Chem. Soc. 110, 2229 (1988).
6. (a) K. Murayama and K. Aoki, Chem. Commun. 607-608 (1998);
7. (b) K.N. Rose, L.J. Barbour, G.W. Orr, and J. Atwood: Chem. Commun. 407-408 (1998);
8. (c) A. Shivanyuk, K. Rissanen, and E. Kolehmainen: Chem. Commun. 1107-1108 (2000);
9. (d) A. Shivanyuk and J. Rebek, Jr.: Chem. Commun. 2374-2375 (2001);
10. (e) H. Mansikkamäki, M. Nissinen, C.A. Schalley, and K. Rissanen: New. J. Chem. 27, 88 (2003);
11. (f) H. Mansikkamäki, M. Nissinen, and K. Rissanen: Chem. Commun. 1902-1903 (2002).
12. (a) L.R. MacGillvray and J.L. Atwood: Nature 389, 469 (1997);
13. (b) A. Shivanyuk and J. Rebek, Jr.: Chem. Commun. 2424 (2001);
14. (c) A. Shivanyuk and J. Rebek, Jr.: Proc. Natl. Acad. Sci. USA 98, 7662 (2001);
15. (d) L. Avram and Y. Cohen: Org. Lett. 4, 4365 (2002);
16. (e) L. Avram and Y. Cohen: J. Am. Chem. Soc. 124, 15148 (2002);
17. (f) A. Shivanyuk and J. Rebek, Jr.: J. Am. Chem. Soc. 124, 12074 (2002);
18. (g) A. Schivanyuk and J. Rebek, Jr.: J. Am. Chem. Soc. 125, 3432 (2003);
19. (h) T. Gerkensmeier, W. Iwanek, C. Agena, R. Fröhlich, S. Kotila, C. Näther, and J. Mattay: Eur. J. Org. Chem. 2257 (1999).
20. H. Mansikkamaki, M. Nissinen, and K. Rissanen: Angew. Chem. 116, 1263 (2004);
21. Angew. Chem. Int. Ed. 43, 1243 (2004).
22. M. Luostarinen, A. Shivanyuk, and K. Rissanen: Org. Lett. 26, 4141 (2001).
23. A. Schivanyuk, C. Schmidt, V. Böhmer, E. Paulus, O. Lukin, and W. Vogt: J. Am. Chem. Soc. 120, 4319 (1998).
24. C. Schmidt, E. Paulus, V. Böhmer, and W. Vogt: New J. Chem. 25, 374 (2001).
25. C. White and J. Burnett: J. Chromatogr. A 1074, 175 (2005).
26. (a) H.J. Schneider, D. Güttes, and U. Schneider: Angew. Chem. 98, 635 (1986);
27. Angew. Chem. Int. Ed. 25, 647 (1986);
28. (b) H.J. Schneider: Angew. Chem. 103, 1419 (1991);
29. Angew. Chem. Int. Ed. 30, 1417 (1991);
30. (c) J.L. Atwood and A. Szumna: J. Am. Chem. Soc. 124, 10646 (2002).
31. H. Mansikkamäki, M. Nissinen, and K. Rissanen: Cryst. Eng. Comm. 7, 519 (2005).
32. H. Mansikkamäki, C.A. Schalley, M. Nissinen, and K. Rissanen: New J. Chem. 29, 116 (2005).
33. For more recent reviews, see: (a) M. Przybylski and M.O. Glocker: Angew. Chem. 108, 878 (1996);
34. Angew. Chem. Int. Ed. 35, 806 (1996);
35. (b) J.S. Brodbelt: Int. J. Mass Spectrom. 200, 57 (2000);
36. (c) C.A. Schalley: Int. J. Mass Spectrom. 194, 11 (2000);
37. (d) C.B. Lebrilla: Acc. Chem. Res. 34, 653 (2001);
38. (e) C.A. Schalley: Mass Spectrom. Rev. 20, 253 (2001).
39. M. Sawada: Mass Spectrom. Rev. 16, 73 (1997).
40. (a) C. Garcia, J. Guyot, G. Jeminet, E. Leize-Wagner, H. Nierengarten, and A. Van Dorsselaer: Tetrahedron Lett. 40, 4997 (1999);
41. (b) H. Nierengarten, E. Leize, C. Garcia, G. Jeminet, and A. Van Dorsselaer: Analysis 28, 259 (2000).
42. (a) C.A. Schalley, R.K. Castellano, M.S. Brody, D.M. Rudkevich, G. Siuzdak, and J. Rebek, Jr.: J. Am. Chem Soc. 121, 4568 (1999);
43. (b) M.S. Brody, D.M. Rudkevich, C.A. Schalley, and J. Rebek, Jr.: Angew. Chem. 111, 1738 (1999);
44. Angew. Chem. Int. Ed. 38, 1640 (1999);
45. (c) A. Lützen, A.R. Renslo, C.A. Schalley, B.M. O'Leary, and J. Rebek, Jr.: J. Am. Chem. Soc. 121, 7455 (1999);
46. (d) B.M. O'Leary, T. Szabo, N. Svenstrup, C.A. Schalley, A. Lützen, J. Rebek, Jr.: J. Am. Chem. Soc. 123, 11519 (2001);
47. (e) M. Makinen, P. Vainiotalo, and K. Rissanen: J. Am. Soc. Mass. Spectrom. 13, 851 (2002);
48. (f) A. Tafi, B. Botta, M. Botta, G.D. Monache, A. Filippi, and M. Speranza: Chem. Eur. J. 10, 4126 (2004).
49. M. Sawada, Y. Takai, H. Hamada, S. Hirayama, T. Kaneda, T. Tankaka, K. Kamada, T. Mizooku, S. Takeuchi, K. Ueno, K. Hirose, Y. Tobe, and K. Naemura: J. Am. Chem. Soc. 117, 7726 (1995).
50. A. Mehdizadeh, M.C. Letzel, M. Klaes, C. Agena, and J. Mattay: Eur. J. Mass Spectrom. 10, 649 (2004).
51. M. Gacek and K. Undheim: Tetrahedron 29, 863 (1973).
52. Spartan 04, Wavefunction Inc., 18401 Von Karman Ave, Irvine/CA, USA.
53. The Program Chemical Kinetics Simulator 1.01 is available online from W. D. Hinsberg, F. A. Houle: https://www.almaden.ibm.com/st/computational_science/ ck/msim/ (August 2004).