Synthesis of redox active large macrocyclic hosts and the recognition of secondary ammonium salts

Tetrahedron

Volumn 59, Issue 5, 2003, Pages 639-647

  Nabeshima, Tatsuya ^a   Nishida, Daisuke ^a   Saiki, Toshiyuki ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Crown ethers; Disufide; Redox reactions; Thiol

Indexed keywords

AMMONIUM DERIVATIVE; MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL BINDING; CYCLIZATION; MOLECULAR RECOGNITION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037467685     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01532-6     Document Type: Article

References (23)

1. (a) Amabilino D.B., Stoddart J.F. Chem. Rev. 95:1995;2725-2828
2. (b) Sauvage J.-P. Acc. Chem. Res. 31:1998;611-619
3. (c) Blanco M.-J., Jiménez M.C., Chambron J.-C., Heitz V., Linke M., Sauvage J.-P. Chem. Soc. Rev. 28:1999;293-305.
4. (a) Lehn J.-M. Supramolecular Chemistry. 1995;VCH, Weinheim,
5. (b) Balzani V., Credi A., Raymo F.M., Stoddart J.F. Angew. Chem., Int. Ed. 39:2000;3348-3391.
6. Izatt R.M., Pawlak K., Bradshaw J.S., Bruening R.L. Chem. Rev. 91:1991;1721-2085.
7. (a) Raban M., Greenblatt J., Kandil F. J. Chem. Soc., Chem. Commun. 1983;1409-1411
8. (b) Shinkai S., Inuzuka K., Miyazaki O., Manabe O. J. Am. Chem. Soc. 107:1985;3950-3955
9. (c) Nabeshima T., Sakiyama A., Yagyu A., Furukawa N. Tetrahedron Lett. 30:1989;5287-5288
10. (d) Nabeshima T., Furusawa H., Yano Y. Angew. Chem., Int. Ed. Engl. 33:1994;1750-1751
11. (e) Nabeshima T., Furusawa H., Tsukuda N., Shinnai T., Haruyama T., Yano Y. Heterocycles. 41:1995;655-659
12. (f) Graubaum H., Tittelbach F., Lutze G., Gloe K., Mackrodt M. J. Prakt. Chem. 339:1997;55-58
13. (g) Nabeshima T., Nishida D. Tetrahedron Lett. 43:2002;5719-5722.
14. Nabeshima T., Nishida D., Horn E.Z. Kristallogr. NCS. 216:2001;80-82.
15. Similar downfield shifts of the benzyl protons of benzylammonium derivatives are observed upon complexation of dibenzocrown and benzocrown ethers with the ammonium guests. (a) Ashton P.R., Campbell P.J., Chrystal E.J.T., Glink P.T., Menzer S., Philp D., Spencer N., Stoddart J.F., Tasker P.A., Williams D.J. Angew. Chem., Int. Ed. Engl. 34:1995;1865-1869 (b) Ashton P.R., Chrystal E.J.T., Glink P.T., Menzer S., Schiavo C., Spencer N., Stoddart J.F., Tasker P.A., White A.J.P., Williams D.J. Chem. Eur. J. 2:1996;709-728 (c) Dykes G.M., Smith D.K., Seeley G.J. Angew. Chem., Int. Ed. 41:2002;3254-3257.
16. Similar downfield shifts of the benzyl protons of benzylammonium derivatives are observed upon complexation of dibenzocrown and benzocrown ethers with the ammonium guests. (a) Ashton P.R., Campbell P.J., Chrystal E.J.T., Glink P.T., Menzer S., Philp D., Spencer N., Stoddart J.F., Tasker P.A., Williams D.J. Angew. Chem., Int. Ed. Engl. 34:1995;1865-1869 (b) Ashton P.R., Chrystal E.J.T., Glink P.T., Menzer S., Schiavo C., Spencer N., Stoddart J.F., Tasker P.A., White A.J.P., Williams D.J. Chem. Eur. J. 2:1996;709-728 (c) Dykes G.M., Smith D.K., Seeley G.J. Angew. Chem., Int. Ed. 41:2002;3254-3257.
17. Similar downfield shifts of the benzyl protons of benzylammonium derivatives are observed upon complexation of dibenzocrown and benzocrown ethers with the ammonium guests. (a) Ashton P.R., Campbell P.J., Chrystal E.J.T., Glink P.T., Menzer S., Philp D., Spencer N., Stoddart J.F., Tasker P.A., Williams D.J. Angew. Chem., Int. Ed. Engl. 34:1995;1865-1869 (b) Ashton P.R., Chrystal E.J.T., Glink P.T., Menzer S., Schiavo C., Spencer N., Stoddart J.F., Tasker P.A., White A.J.P., Williams D.J. Chem. Eur. J. 2:1996;709-728 (c) Dykes G.M., Smith D.K., Seeley G.J. Angew. Chem., Int. Ed. 41:2002;3254-3257.
18. Edwin W. Chem. Ber. 118:1985;4439-4452.
19. Jullien L., Canceill J., Lacombe L., Lehn J.-M. J. Chem. Soc., Perkin Trans. 2. 1994;989-1002.
20. Merz A., Eichner M., Tomahogh R. Liebigs Ann. Chem. 1981;1774-1784.
21. Asakawa M., Ashton P.R., Balzani V., Boyd S.E., Credi A., Mattersteig G., Menzer S., Montalti M., Raymo F.M., Ruffilli C., Stoddart J.F., Venturi M., Williams D.J., Eur. J. Org. Chem. 1999;985-994.
22. Kopolow S., Hogen Esch T.E., Smid J. Macromolecules. 6:1973;133-142.
23. Newcomb M., Moore S.S., Cram D.J. J. Am. Chem. Soc. 99:1977;6405-6410.