The conformational analysis of 14-membered macrocyclic ethers

Tetrahedron

Volumn 56, Issue 10, 2001, Pages 1281-1297

  Clyne, Dean S ^a   Weiler, Larry ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Conformation; Ethers; Macrocycles; NMR

Indexed keywords

ETHER DERIVATIVE; MACROCYCLIC COMPOUND;

ANISOTROPY; ARTICLE; CALCULATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENERGY; ENTROPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 0343550407     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00050-8     Document Type: Article

References (36)

1. (a) Keller, T. H.; Neeland, E. G.; Rettig, S.; Trotter, J.; Weiler, L. J. Am. Chem. Soc. 1988, 110, 7858.
2. (b) Keller, T. H.; Weiler, L. J. Am. Chem. Soc. 1990, 112, 450.
3. (c) Neeland, E. G.; Ounsworth, J. P.; Sims, R. J.; Weiler, L. J. Org. Chem. 1994, 59, 7383.
4. (d) Neeland, E. G.; Sharadendu, A.; Weiler, L. Tetrahedron Lett. 1996, 37, 5069.
5. Meyer W.L., Taylor P.W., Reed S.A., Leister M.C., Schneider H.-J., Schmidt G., Evans F.E., Levine R.A. J. Org. Chem. 57:1992;291.
6. Clyne D.S., Weiler L. Tetrahedron. 55:1999;13659.
7. (a) Dale, J. J. Chem. Soc. 1963, 93.
8. (b) Dale, J. Angew. Chem., Int. Ed. Engl. 1966, 5, 1000.
9. Dale J. Acta Chem. Scand. 27:1973;1115.
10. (a) Anet, F. A. L.; Cheng, K. J. Am. Chem. Soc. 1975, 97, 2420.
11. (b) Anet, F. A. L.; Rawdah, T. N. J. Am. Chem. Soc. 1978, 100, 7810.
12. See Ref. 5 and Neeland, E.G. PhD Thesis, University of British Columbia, 1987.
13. Groth P. Acta Chem. Scand. A. 30:1976;155.
14. (a) Anet, F. A. L.; Cheng, A. K.; Wagner, J. J. J. Am. Chem. Soc. 1972, 94, 9250.
15. (b) Drotloff, H.; Rotter, H.; Emeis, D.; Moeller, M. J. Am. Chem. Soc. 1987, 109, 7797.
16. Shannon D.L., Strauss H.L., Snyder R.G., Elliger C.A., Mattice W.L. J. Am. Chem. Soc. 89:1989;1947.
17. Bassi I.W., Scordamaglia R., Fiore L. J Chem. Soc., Perkin Trans. 2. 1972;1726.
18. Groth P. Acta Chem. Scand. A. 29:1975;374.
19. Groth P. Acta Chem. Scand. A. 33:1979;503.
20. Dale J. Tetrahedron. 30:1974;1683.
21. ApSimon J.W., Craig W.G., Demarco P.V., Mathieson D.W., Saunders L., Whalley W.B. Tetrahedron. 23:1967;2339.
22. Cheney B.V. J. Am. Chem. Soc. 90:1968;5386.
23. Bondi A. J. Phys. Chem. 68:1964;441.
24. (a) Gschwendtner, W.; Schneider, H.-J. J. Org. Chem. 1980, 45, 3507.
25. (b) Schneider, H.-J.; Buchheit, U.; Becker, N.; Schmidt, G.; Siehl, U. J. Am. Chem. Soc. 1985, 107, 7027.
26. Bovey F.A., Hood F.P. III, Anderson E.W., Kornegay R.L. J. Chem. Phys. 41:1964;2041.
27. Lambert J.B., Mixan C.E., Johnson D.H. J. Am. Chem. Soc. 95:1973;4634.
28. Lambert J.B., Goldstein J.E. J. Am. Chem. Soc. 99:1977;5689.
29. Friebolin H. Basic One- and Two-Dimensional NMR Spectroscopy. 1991;263-272 VCH, New York.
30. Anet F.A.L., Cheng A.K., Wagner J.J. J. Am. Chem. Soc. 94:1972;9250.
31. Dale J. Acta Chem. Scand. 27:1973;1130.
32. Wiberg K.B., Boyd R.H. J. Am. Chem. Soc. 94:1972;8426.
33. Dale J. Top. Stereochem. 9:1976;199.
34. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C. J. Comput. Chem. 11:1990;440.
35. Allinger N.L. J. Am. Chem. Soc. 99:1977;8127.
36. Allinger N.L., Yuh Y.H., Lii J.-H. J. Am. Chem. Soc. 111:1989;8551.