Solution Studies of Sulfur-Stabilized Lithiated Allylic Carbanions: HOESY (6Li-1H) NMR Spectroscopy of Lithiated (E)-1-(t-Butylthio)but-2-ene and (E)-1-(Phenylthio)but-2-ene

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 7, 1996, Pages 2025-2029

  Glendenning, Lionel ^a,b   Bampos, Nick ^a,c   Field, Leslie D ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b TOHOKU UNIVERSITY   (Japan)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013492548     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.2025     Document Type: Article

References (39)

1. For reviews of heteroatom stabilized allylic carbanions see Y. Yamamoto in : a) Y. Yamamoto and N. Asao, Chem. Rev., 93, 2207 (1993); Y. Yamamoto, "Comprehensive Organic Synthesis," ed by C. H. Heathcock, Pergamon Press, Oxford (1990), Vol. 2, p. 55; Y. Yamamoto, H. Yatagai, Y. Saito, and K. Maruyama, J. Org. Chem., 49, 1096 (1984); and also, b) D. Hoppe, Angew. Chem., Int. Ed. Engl., 23, 932 (1984).
2. For reviews of heteroatom stabilized allylic carbanions see Y. Yamamoto in : a) Y. Yamamoto and N. Asao, Chem. Rev., 93, 2207 (1993); Y. Yamamoto, "Comprehensive Organic Synthesis," ed by C. H. Heathcock, Pergamon Press, Oxford (1990), Vol. 2, p. 55; Y. Yamamoto, H. Yatagai, Y. Saito, and K. Maruyama, J. Org. Chem., 49, 1096 (1984); and also, b) D. Hoppe, Angew. Chem., Int. Ed. Engl., 23, 932 (1984).
3. For reviews of heteroatom stabilized allylic carbanions see Y. Yamamoto in : a) Y. Yamamoto and N. Asao, Chem. Rev., 93, 2207 (1993); Y. Yamamoto, "Comprehensive Organic Synthesis," ed by C. H. Heathcock, Pergamon Press, Oxford (1990), Vol. 2, p. 55; Y. Yamamoto, H. Yatagai, Y. Saito, and K. Maruyama, J. Org. Chem., 49, 1096 (1984); and also, b) D. Hoppe, Angew. Chem., Int. Ed. Engl., 23, 932 (1984).
4. For reviews of heteroatom stabilized allylic carbanions see Y. Yamamoto in : a) Y. Yamamoto and N. Asao, Chem. Rev., 93, 2207 (1993); Y. Yamamoto, "Comprehensive Organic Synthesis," ed by C. H. Heathcock, Pergamon Press, Oxford (1990), Vol. 2, p. 55; Y. Yamamoto, H. Yatagai, Y. Saito, and K. Maruyama, J. Org. Chem., 49, 1096 (1984); and also, b) D. Hoppe, Angew. Chem., Int. Ed. Engl., 23, 932 (1984).
5. D. Seebach, T. Maetzke, R. K. Haynes, M. N. Paddon-Row, and S. S. Wong, Helv. Chim. Acta, 71, 299 (1988).
6. H-J. Gais, J. Volhardt, and H. J. Lindner, Angew. Chem., Int. Ed. Engl, 25, 939 (1986).
7. G. Chassaing and A. Marquet, Tetrahedron, 34, 1399 (1978).
8. L. Glendenning, L. D. Field, and R. K. Haynes, Bull. Chem. Soc. Jpn., 68, 2739 (1995).
9. L. Glendenning, Ph. D. Thesis, University of Sydney, 1992.
10. a) M. R. Binns, R. K. Haynes, T. L. Houston, and W. R. Jackson, Tetrahedron Lett., 21, 573 (1980)
11. b) M. R. Binns and R. K. Haynes, J. Org. Chem., 46, 3790 (1981).
12. M. R. Binns, O. L. Chai, R. K. Haynes, A. A. Katsifis, P. A. Schober, and S. C. Vonwiller, Tetrahedron Lett., 26, 1569 (1985).
13. For examples of the application of HOESY spectroscopy to other heteronuclei see : a) C. Yu and G. C. Levy, J. Am. Chem. Soc., 105, 6994 (1983) b) C. Yu and G. C. Levy, J. Am. Chem. Soc., 106, 6533 (1984).
14. For examples of the application of HOESY spectroscopy to other heteronuclei see : a) C. Yu and G. C. Levy, J. Am. Chem. Soc., 105, 6994 (1983) b) C. Yu and G. C. Levy, J. Am. Chem. Soc., 106, 6533 (1984).
15. a) W. Bauer, T. Clark, and P. v. R. Schleyer, J. Am. Chem. Soc., 109, 970 (1987)
16. b) W. Bauer and P. v. R. Schleyer, Magn. Reson. Chem., 26, 827 (1988)
17. c) W. Bauer and P. v. R. Schleyer, J. Am. Chem. Soc., 111, 7191 (1989)
18. d) W. Bauer, G. Muller, R. Pi, and P. v. R. Schleyer, Angew. Chem., Int. Ed. Engl., 25, 1103 (1986)
19. e) W. Bauer, in "Lithium Chemistry: A Theoretical and Experimental Overview," ed by P. v. R. Schleyer and A. -M. Sapse, J. Wiley and Sons (Pub.), New York (1995), Chap. 5, pp. 125-172.
20. For a review of the NMR spectroscopic techniques used in organolithium structural elucidation see: H. Gunther, D. Moskau, P. Bast, and D. Schmalz, Angew. Chem., Int. Ed. Engl., 26, 1212 (1987).
21. P. L. Rinaldi, F. J. Swiecinski, and M. Tokles, J. Magn. Reson., 91, 222 (1991).
22. M. A. Nichols, A. T. McPhail, and E. M. Arnett, J. Am. Chem. Soc., 113, 6222 (1991).
23. a) G. Hilmersson and O. Davidsson, Oragnometallics, 14, 912 (1995)
24. b) G. Hilmersson and Ö. Davidsson, J. Organomet. Chem., 489, 175 (1995).
25. P. L. Rinaldi, J. Am. Chem. Soc., 105, 5167 (1983).
26. 10d)
27. a) J. H. Noggle and R. E. Schirmer, in "The Nuclear Overhauser Effect," Academic Press, New York (1971)
28. b) D. Neuhaus and M. Williamson, in "The Nuclear Overhauser Effect in Structural and Conformational Analysis," VCH Publishers, New York (1989).
29. a) G. Boche, Angew. Chem., Int. Ed. Engl., 28, 277 (1989), and references cited therein
30. b) R. E. Mulvey, Chem. Soc. Rev., 20, 167 (1991)
31. c) A. G. Abatjoglou, E. L. Eliel, and L. F. Kuyper, J. Am. Chem. Soc., 99, 8262 (1977).
32. H. Gilman, E. A. Zoellner, and W. M. Selby, J. Am. Chem. Soc., 55, 1252 (1933); H. Gilman, W. Langham, and F. W. Moore, J. Am. Chem. Soc., 62, 2327 (1940); H. Gilman, J. A. Beel, C. G. Brannen, M. W. Bullock, G. E. Dunn, and L. S. Miller, J. Am. Chem. Soc., 71, 1499 (1949); C. W. Kamienski and D. L. Esmay, J. Am. Chem. Soc., 25, 1807 (1960); L. J. Tyler, L. H. Sommer, and F. C. Whitmore, J. Am. Chem. Soc., 70, 2876 (1948).
33. H. Gilman, E. A. Zoellner, and W. M. Selby, J. Am. Chem. Soc., 55, 1252 (1933); H. Gilman, W. Langham, and F. W. Moore, J. Am. Chem. Soc., 62, 2327 (1940); H. Gilman, J. A. Beel, C. G. Brannen, M. W. Bullock, G. E. Dunn, and L. S. Miller, J. Am. Chem. Soc., 71, 1499 (1949); C. W. Kamienski and D. L. Esmay, J. Am. Chem. Soc., 25, 1807 (1960); L. J. Tyler, L. H. Sommer, and F. C. Whitmore, J. Am. Chem. Soc., 70, 2876 (1948).
34. H. Gilman, E. A. Zoellner, and W. M. Selby, J. Am. Chem. Soc., 55, 1252 (1933); H. Gilman, W. Langham, and F. W. Moore, J. Am. Chem. Soc., 62, 2327 (1940); H. Gilman, J. A. Beel, C. G. Brannen, M. W. Bullock, G. E. Dunn, and L. S. Miller, J. Am. Chem. Soc., 71, 1499 (1949); C. W. Kamienski and D. L. Esmay, J. Am. Chem. Soc., 25, 1807 (1960); L. J. Tyler, L. H. Sommer, and F. C. Whitmore, J. Am. Chem. Soc., 70, 2876 (1948).
35. H. Gilman, E. A. Zoellner, and W. M. Selby, J. Am. Chem. Soc., 55, 1252 (1933); H. Gilman, W. Langham, and F. W. Moore, J. Am. Chem. Soc., 62, 2327 (1940); H. Gilman, J. A. Beel, C. G. Brannen, M. W. Bullock, G. E. Dunn, and L. S. Miller, J. Am. Chem. Soc., 71, 1499 (1949); C. W. Kamienski and D. L. Esmay, J. Am. Chem. Soc., 25, 1807 (1960); L. J. Tyler, L. H. Sommer, and F. C. Whitmore, J. Am. Chem. Soc., 70, 2876 (1948).
36. H. Gilman, E. A. Zoellner, and W. M. Selby, J. Am. Chem. Soc., 55, 1252 (1933); H. Gilman, W. Langham, and F. W. Moore, J. Am. Chem. Soc., 62, 2327 (1940); H. Gilman, J. A. Beel, C. G. Brannen, M. W. Bullock, G. E. Dunn, and L. S. Miller, J. Am. Chem. Soc., 71, 1499 (1949); C. W. Kamienski and D. L. Esmay, J. Am. Chem. Soc., 25, 1807 (1960); L. J. Tyler, L. H. Sommer, and F. C. Whitmore, J. Am. Chem. Soc., 70, 2876 (1948).
37. M. R. Winkle, J. M. Lansinger, and R. C. Ronald, J. Chem. Soc., Chem. Commun., 1980, 87.
38. For a recently published invaluable aid in the preparation of organolithium reagents, see: M. Schlosser, in "Organometallics in Synthesis, A Manual," ed by M. Schlosser, John Wiley & Sons (Pub.), New York (1994), Chap. 1, pp. 1-166.
39. R. L. Vold, J. S. Waugh, M. P. Klein, and D. E. Phelps, J. Chem. Phys., 48, 3831 (1968).