Dipole-Stabilized Carbanions from Thioesters. Evidence for Stabilization by the Carbonyl Group

Journal of the American Chemical Society

Volumn 100, Issue 17, 1978, Pages 5428-5436

  Reitz, David B ^a   Beak, Peter ^a   Farney, Robert F ^a   Helmick, Larry S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009648751     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00485a030     Document Type: Article

References (60)

1. P. Beak and B. G. McKlnnie, J. Am. Chem. Soc., 99, 5213 (1977).
2. P. Beak, B. G. McKinnie and D. B. Reitz, Tetrahedron Lett., 1839 (1977).
3. P. Beak and D. B. Reitz, Chem. Rev., 78, 275 (1978).
4. D. Seebach and W. Lubosch, Angew. Chem., Int. Ed. Engl., 15, 313 (1976).
5. R. Schlecker and D. Seebach, Helv. Chim. Acta, 60, 1459 (1977).
6. K. Hirai, H. Matsuda and Y. Kishida, Tetrahedron Lett., 4359 (1971);.
7. C. R. Johnson, A. Nakanishi, N. Nakanishi and K. Tanaka, Tetrahedron Lett., 2865 (1975).
8. A. I. Meyers and M. E. Ford, Tetrahedron Lett., 2861 (1975);.
9. A. I. Meyers and M. E. Ford, J. Org. Chem., 41, 1735 (1976).
10. K. Hirai and Y. Kishida, Heterocycles, 2, 185 (1974).
11. C. R. Johnson and K. Tanaka, Synthesis, 413 (1976).
12. D. Hoppe, Angew. Chem., Int. Ed. Engl., 14, 424 (1975).
13. K. Hirai and Y. Kishida, Tetrahedron Lett., 2743 (1972).
14. E. Negishi, T. Yoshida, A. Silveira, Jr. and B. L. Chiou, J. Org. Chem., 40, 814 (1975).
15. P. Beak and R. Farney, J. Am. Chem. Soc., 95, 4771 (1973).
16. R. A. Olofson and C. M. Dougherty, J. Am. Chem. Soc., 95, 582 (1973).
17. R. Kow and M. W. Rathke, J. Am. Chem. Soc., 95, 2715 (1973).
18. C. C. Kissel and_B. Rickborn, J. Org. Chem., 37, 2060 (1972).
19. M. Oki, W.Funakoshi and A. Nakamura, Bull. Chem. Soc. Jpn., 44, 828 (1971).
20. M. Oki and W. Funakoshi, Bull. Chem. Soc. Jpn., 44, 832 (1971).
21. P. Beak, G. R. Brubaker and R. F. Farney, J. Am. Chem. Soc., 98, 3621 (1976).
22. A. Nickon, J. C. Lambert, J. E. Oliver, D. F. Covery and J. Morgan, J. Am. Chem. Soc., 98, 2593 (1976).
23. A. I. Meyers and E. D. Mihelich, J. Org. Chem., 40, 3158 (1975).
24. P. Beak and E. M. Monroe, J. Org. Chem., 34, 589 (1969).
25. J. P. Marino, M. Nelsser and W. Butler.
26. D. W. Slocum and D. I. Sugarman, Adv. Chem. Ser., 130, 222-247 (1974).
27. H. W. Gschwend and A. Hamden, J. Org. Chem., 40, 2008 (1975).
28. P. Beak and R. A. Brown, J. Org. Chem., 42, 1823 (1977).
29. P. Beak and C. J.
30. R. E. Ludt, J. S. Griffiths, K. N. McGrath and C. R. Hauser, J. Org. Chem., 38, 1668 (1973).
31. D. J. Cram, Academic Press, New York, N.Y., 1965.
32. D. J. Peterson, Organomet. Chem. Rev., Sect. A, 7, 295 (1972).
33. M. Schlosser, Springer-Verlag, West Berlin, 1973, Chapter 2; E. Bunoel, American Elsevier, New York, N.Y., 1975,.
34. S. Wolfe, Acc. Chem. Res., 5, 102 (1972); J. Lehn and G. Wipff, J. Am. Chem. Soc., 98, 7498 (1976).
35. N. D. Epiotis, R. L. Yates, F. Bernardi and S. Wolfe, J. Lehn and G. Wipff, J. Am. Chem. Soc., 98, 5435 (1976).
36. A. Streitwieser, Jr. and J. E. Williams, Jr., J. Lehn and G. Wipff, J. Am. Chem. Soc., 97, 191 (1975).
37. F. G. Bordwell, J. E. Bares, J. E. Bartmess, G. E. Drucker, J. Gerhold, G. J. McCollum, M. Van Der Puy, N. R. Vanier and W. S. Matthews, J. Org. Chem., 42, 326 (1977).
38. F. G. Bordwell, M. Van Der Puy and N. R. Vanier, J. Org. Chem., 41, 1885 (1976).
39. T. M. Dolak and T. A. Bryson, Tetrahedron Lett., 1961 (1971).
40. D. Peterson, J. Org. Chem., 32, 1717 (1967).
41. E. J. Corey and D. Seebach, J. Org. Chem., 31, 4097 (1966).
42. R. Taylor, Tetrahedron Lett., 435 (1975).
43. R. Levine, M. J. Karten and W. M. Kadunce, J. Org. Chem., 40, 1770 (1975).
44. K. Smith, Annu. Rep. Prog. Chem., Sect. B, 72, 189 (1976).
45. G. R. Brubaker and P. Beak, J. Organomet. Chem., 136, 147 (1977),.
46. S. C. Watson and J. F. Eastham, J. Organomet. Chem., 9, 165 (1967).
47. L. S. Pratt and E. E. Reid, J. Am. Chem. Soc., 37, 1934 (1915).
48. R. Mayer, S. Scheithauer and D. Kunz, Chem. Ber., 99, 1393 (1966).
49. R. Otto and R. Luders, Chem. Ber., 13, 1283 (1880).
50. B. Groth, Ark. Kemi, 9, 50 (1924).
51. R. Ireland and J. A. Marshall, J. Org. Chem., 27, 1615 (1962).
52. R. P. Barnes, Org. Synth., 21, 77 (1941).
53. R. C. Fuson and J. Corse, J. Am. Chem. Soc., 60, 2063 (1938).
54. R. C. Fuson and E. C. Horning, J. Am. Chem. Soc., 62, 2962 (1940).
55. M. S. Newman, J. Am. Chem. Soc., 63, 2431 (1941).
56. E. E. Betts and L. R. C. Barclay, Can. J. Chem., 33, 1768 (1955).
57. A. Sieglitz and O. Horn, Chem. Ber., 84, 607 (1951).
58. R. D. Abell, J. Chem. Soc., 79, 928 (1901).
59. J. Braun, Chem. Ber., 45, 1563 (1912).
60. C. L. Arcus and P. A. Hallgarten, J. Chem. Soc., 2987 (1956).