A New Route to Crown Ethers by Ruthenium-Catalyzed Ring Closing Metathesis

Synlett

Volumn 1996, Issue 10, 1996, Pages 1013-1014

  König, Burkhard ^a   Horn, Clemens ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0039658501     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5643     Document Type: Article

References (19)

1. Dietrich, B.; Viout, P.; Lehn, J.-M., Macrocyclic Chemistry VCH: Weinheim, 1993.
2. Gokel, G. In Crown Ethers and Cryptands, Monographs in Supramolecular Chemistry, Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, 1989.
3. Czarnik, A. In Fluorescence Sensors ACS Symposium Series: Washington, 1992.
4. Trost, B. M. Science 1991, 254, 1471-1477.
5. (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452.
6. (b) Schmalz, H.-G. Angew. Chem. 1995, 107, 1981-1984; Angew. Chem. Int. Ed. Engl. 1995, 34, 1983-1987.
7. (b) Schmalz, H.-G. Angew. Chem. 1995, 107, 1981-1984; Angew. Chem. Int. Ed. Engl. 1995, 34, 1983-1987.
8. (c) Enol ethers via metathesis: Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029-4031.
9. For a substituted analog of 3b and 3c see: van Staveren, C. J.; van Erden, J.; van Harkema, F. C. J. M.; Harkema, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 1988, 110, 4994-5008.
10. Synthesis adapted from: Tietze, L. F.; Eicher, Th. Reaktionen und Synthesen Thieme: Stuttgart, 1991, p. 371.
11. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
12. Kleinpeter, E.; Gäbler, M.; Schroth, W.; Mattinen, J.; Pihlaja, K. Magn. Res. Chem. 1988, 26, 387-391.
13. 2 2:98) to yield 140 mg (80%) 3a.
14. The reaction progress and product formation was followed in all experiments by HPLC. Column RP18, MeOH:water 85:15; detection UV.
15. quart) for quarternary carbon atoms.
16. Riemschneider, R.; Kötzsch, H. J. Monatsh. Chem. 1959, 90, 787-791.
17. (a) Inoue, Y.; Wada, K.; Ouchi, M.; Tai, A.; Hakushi, T. Chem. Lett. 1988, 1005-1008. The yield of compound 9 obtained by Sn ring closure is 7%.
18. (b) For related compounds, see: Inoue, Y.; Harino, H.; Koseki, N.; Hakushi, T. J. Org. Chem. 1985, 50, 5151-5156.
19. The effect of added diglyme, triglyme and tetraglyme (1 mol% catalyst, 3 equiv. glycol ether) on the turnover number of 2 was investigated in the conversion of styrene to trans-stilbene. No significant change of the turnover number with added glycol ether was observed.