Stereoelectronic effects in sulfonyl compounds: Axial orientation of an N-methyl group in a six-membered sultam

Canadian Journal of Chemistry

Volumn 76, Issue 2, 1998, Pages 164-170

  King, James Frederick ^a   Yuyitung, Gay ^a   Gill, Manjinder Singh ^a   Stewart, Jeffrey Charles ^a   Payne, Nicholas Charles ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

Generalized anomeric effect; Negative hyperconjugation; Sulfonamides; Sultams; X ray crystallography

Indexed keywords

CONFORMATIONS; MOLECULAR ORIENTATION; MOLECULAR STRUCTURE; SINGLE CRYSTALS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

GENERALIZED ANOMERIC EFFECTS; HYPERCONJUGATION; STEREOELECTRONIC EFFECTS;

SULFUR COMPOUNDS;

EID: 0032000241     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/cjc-76-2-164     Document Type: Article

References (32)

1. J.F. King and M.S. Gill. J. Org. Chem. 61, 7250 (1996).
2. R.U. Lemieux. Pure Appl. Chem. 25, 527 (1971).
3. P.v.R. Schleyer and A.J. Kos. Tetrahedron, 39, 1141 (1983).
4. G. Boche. Angew. Chem. Int. Ed. Engl. 28, 277 (1989).
5. J.S. Grossert, J. Hoyle, T.S. Cameron, S.P. Roe, and B.R. Vincent. Can. J. Chem. 65, 1407 (1987).
6. W.v.E. Doering and L.K. Levy. J. Am. Chem. Soc. 77, 509 (1955).
7. D.W.J. Cruickshank. J. Chem. Soc. 5486 (1961).
8. S. Wolfe, A. Stolow, and L.A. LaJohn. Tetrahedron Lett. 24, 4071 (1983).
9. D.A. Bors and A. Streitwieser, Jr. J. Am. Chem. Soc. 108, 1397 (1986).
10. R. Koch and E. Anders. J. Org. Chem. 59, 4529 (1994).
11. T. Jordan, H.W. Smith, L.L. Lohr, Jr., and W.N. Lipscomb. J. Am. Chem. Soc. 85, 846 (1963).
12. W.B. Jennings and R. Spratt. Chem. Commun. 1418 (1970).
13. J.F. King, K.C. Khemani, S. Skonieczny, and N.C. Payne. J. Chem. Soc. Chem. Commun. 415 (1988).
14. A.C. Hazell. Acta Crystallogr. Sect. B: Struct. Crystallogr. Cryst. Chem. B30, 2724 (1974).
15. J.F. King, K.C. Khemani, S. Skonieczny, and N.C. Paync. Rev. Heteroat. Chem. 1, 80 (1988).
16. R.D. Bindal, J.T. Golab, and J.A. Katzenellenbogen. J. Am. Chem. Soc. 112, 7861 (1990).
17. A. Segre, R. Viterbo, and G. Parisi. J. Am. Chem. Soc. 79, 3503 (1957).
18. H. Booth and J.R. Everett. J. Chem. Soc. Perkin Trans. 2, 255 (1980).
19. A. McIntosh. B.Sc. Thesis, University of Western Ontario. 1990.
20. A Camerman and N. Camerman. Can. J. Chem. 53, 2194 (1975).
21. E.L. Eliel and S. Wilen. In Stereochemistry of organic compounds. John Wiley & Sons, New York. 1994. p. 697.
22. S. Sato, T. Yoshioka, and C. Tamura. Acta Crystallogr. Sect. B: Struct. Crystallogr. Cryst. Chem. B31, 1385 (1975).
23. L.G. Vorontsova. Zh. Strukt. Khim. 7, 280 (1966); Chem. Abstr. 65, 4761a (1966).
24. L.G. Vorontsova. Zh. Strukt. Khim. 7, 280 (1966); Chem. Abstr. 65, 4761a (1966).
25. S. Li, A.J. Kirby, and P. Deslongchamps. Tetrahedron Lett. 34, 7757 (1993); S. Li and P. Deslongchamps. Tetrahedron Lett. 34, 7759 (1993).
26. S. Li, A.J. Kirby, and P. Deslongchamps. Tetrahedron Lett. 34, 7757 (1993); S. Li and P. Deslongchamps. Tetrahedron Lett. 34, 7759 (1993).
27. Z.R. Guo. Ph.D. Thesis. University of Western Ontario. 1993; J.F. King, M. Li, and Z.R. Guo. 79th Canadian Society of Chemistry Conference, St John's, Nfld., June 1996. Abstract 77.
28. Z.R. Guo. Ph.D. Thesis. University of Western Ontario. 1993; J.F. King, M. Li, and Z.R. Guo. 79th Canadian Society of Chemistry Conference, St John's, Nfld., June 1996. Abstract 77.
29. XSCANS users manual, Version 2.1. Siemens X-ray Analytical, Madison, Wis. 1994.
30. Enraf-Nonius EXPRESS users manual, Enraf-Nonius, Delft, The Netherlands. 1990.
31. G.M. Sheldrick. SHELXS. Program for solution of crystal structures. University of Göttingen, Germany. 1986.
32. G.M. Sheldrick. SHELX93. Program for refinement of crystal structures. University of Göttingen, Germany. 1993