l-Lysine-linked anthracenophane derived from thermodynamically controlled intermediates

Tetrahedron Letters

Volumn 48, Issue 18, 2007, Pages 3225-3228

  Kutsumizu, Ryuta ^a   Shinmori, Hideyuki ^a   Takeuchi, Toshifumi ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

Anthracene; Cation interaction; Host guest system; Macrocycles; Silver ion

Indexed keywords

ANTHRACENE DERIVATIVE; ESTER DERIVATIVE; LYSINE; METAL; SILVER;

ARTICLE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CYCLIZATION; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 34047117260     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.028     Document Type: Article

References (47)

1. Dietrich B., Viout P., and Lehn J.-M. Macrocyclic Chemistry: Aspects of Organic and Inorganic Supramolecular Chemistry (1993), VCH, Weinheim
2. Schrader T., and Hamilton A.D. Functional Synthetic Receptors (2005), Wiley-VCH, Weinheim
3. Aricó F., Chang T., Cantrill S.J., Khan S.I., and Stoddart J.F. Chem. Eur. J. 11 (2005) 4655-4666
4. Fujita M., Tominaga M., Hori A., and Therrien B. Acc. Chem. Res. 38 (2005) 371-380
5. Franceconi O., Ienco A., Moneti G., Nativi C., and Roelens S. Angew. Chem., Int. Ed. 45 (2006) 6693-6696
6. Schmidtchen F.P., and Berger M. Chem. Rev. 97 (1997) 1609-1646
7. Baudoin O., Gonnet F., Teulade-Fichou M.-P., Vigneron J.-P., Tabet J.-C., and Lehn J.-M. Chem. Eur. J. 5 (1999) 2762-2771
8. Jantos K., Rodriguez R., Ladame S., Shirude P.S., and Balasubramanian S. J. Am. Chem. Soc. 128 (2006) 13662-13663
9. Weinelt F., and Schneider H.-J. J. Org. Chem. 56 (1991) 5527-5535
10. Branda N., Wyler R., and Rebek Jr. J. Science 263 (1994) 1267-1268
11. Timmerman P., Vreekamp R.H., Hulst R., Verboom W., Reinhoudt D.N., Rissanen K., Udachin K.A., and Ripmeester J. Chem. Eur. J. 3 (1997) 1823-1832
12. Xing L., Ziener U., Suntherland T.C., and Cuccia L.A. Chem. Commun. (2005) 5751-5753
13. McKinlay R.M., Thallapally P.K., Cave G.W.V., and Atwood J.L. Angew. Chem., Int. Ed. 44 (2005) 5733-5736
14. Ma C., Zhang Q., Zhang R., and Wang D. Chem. Eur. J. 12 (2006) 420-428
15. Mukherjee P.S., Das N., Kryschenko Y.K., Arif A.M., and Stang P.J. J. Am. Chem. Soc. 126 (2004) 2464-2473
16. Lehn J.-M. Chem. Eur. J. 5 (1999) 2455-2463
17. Rowan S.J., Cantrill S.J., Cousins G.R.L., Sanders J.K.M., and Stoddart J.F. Angew. Chem., Int. Ed. 41 (2002) 898-952
18. Lam R.T.S., Belenguer A., Roberts S.L., Naumann C., Jarrosson T., Otto S., and Sanders J.K.M. Science 308 (2005) 667-669
19. Cacciapaglia R., Stefano S.D., and Mandolini L. J. Am. Chem. Soc. 127 (2005) 13666-13671
20. Liu X., and Warmuth R. J. Am. Chem. Soc. 128 (2006) 14120-14127
21. Diederich F. Angew. Chem., Int. Ed. 27 (1988) 362-386
22. Diederich F. Cyclophanes (1991), The Royal Society of Chemistry, Cambridge, UK
23. Jeppesen J.O., Nielsen M.B., and Becher J. Chem. Rev. 104 (2004) 5115-5132
24. Kawase T. Angew. Chem., Int. Ed. 44 (2005) 7334-7336
25. Neelakandan P.P., Hariharan M., and Ramaiah D. J. Am. Chem. Soc. 128 (2006) 11334-11335
26. Liu R., and Still W.C. Tetrahedron Lett. 34 (1993) 2573-2576
27. You J.-S., Yu X.-Q., Zhang G.-L., Xiang Q.-X., Lan J.-B., and Xie R.-G. Chem. Commun. (2001) 1816-1817
28. Gibson S.E., and Lecci C. Angew. Chem., Int. Ed. 45 (2006) 1364-1377
29. Pierre J.L., Baret P., Chautemps P., and Armand M. J. Am. Chem. Soc. 103 (1981) 2986-2988
30. Kang H.C., Hanson A.W., Eaton B., and Boekelheide V. J. Am. Chem. Soc. 107 (1985) 1979-1985
31. Heirtzler F.R., Hopf H., Jones P.G., Bubenitschek P., and Lehne V. J. Org. Chem. 58 (1993) 2781-2784
32. Xu W., Puddephatt R.J., Muir K.W., and Torabi A.A. Organometallics 13 (1994) 3054-3062
33. Ma J.C., and Dougherty D.A. Chem. Rev. 97 (1997) 1303-1324
34. Mascal M., Hansen J., Blake A.J., and Li W.-S. Chem. Commun. (1998) 355-356
35. Lindeman S.V., Rathore R., and Kochi J.K. Inorg. Chem. 39 (2000) 5707-5716
36. Hong B.H., Bae S.C., Lee C.-W., Jeong S., and Kim K.S. Science 294 (2001) 348-351
37. Iyoda M., Horino T., Takahashi F., Hasegawa M., Yoshida M., and Kuwatani Y. Tetrahedron Lett. 42 (2001) 6883-6886
38. Kang J., Choi M., Kwon J.Y., Lee E.Y., and Yoon J. J. Org. Chem. 67 (2002) 4384-4386
39. Rathore R., Chebny V.J., and Abdelwahed S.H. J. Am. Chem. Soc. 127 (2005) 8012-8013
40. Chou T.-C., Hwa C.-L., Lin J.-J., Liao K.-C., and Tseng J.-C. J. Org. Chem. 70 (2005) 9717-9726
41. Klanderman B.H. J. Org. Chem. 31 (1966) 2618-2620
42. + 725.9376, found 725.7119.
43. MALDI-TOF-MS instrument settings; matrix: No-matrix, Polarity: Positive.
44. 2 = 0.1092 [I > 2σ(I)].
45. + 723.9186, found 723.7119.
46. Job A. Ann. Chim. 9 (1928) 113-203
47. The binding isotherms were shown in Supplementary data.