Dipole Stabilized Carbanions. Reactions of Benzoate Esters with Lithium 2,2,6,6-Tetramethylpiperidide

Journal of Organic Chemistry

Volumn 40, Issue 8, 1975, Pages 1094-1098

  Upton, Charles J ^a   Beak, Peter ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005779079     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00896a022     Document Type: Article

References (48)

1. P. Beak and R. Farney, J. Am. Chem. Soc., 95, 4771 (1973)
2. D. A. Evans, G. C. Andrews, and B. Buckvalter, J. Am. Chem. Soc., 96, 5560 (1974)
3. W. C. Still and T. C. MacDonald, J. Am. Chem. Soc., 96, 5561 (1974)
4. U. Schöllkopf and P. Hässel, Justus Liebigs Ann. Chem., 763, 208 (1972)
5. J. E. Baldwin, G. A. Höfle, and O. W. Leiner, J. Am. Chem. Soc., 96, 7125 (1974)
6. G. Stortz and B. Carbel, C. R. Acad. Sci., 276, 1807 (1973)
7. R. A. Olofson and C. M. Dougherty, J. Am. Chem. Soc., 95, 581 (1973)
8. C. L. Kissel and B. Rickborn, J. Org. Chem., 37, 2060 (1972)
9. W. Sahm, E. Schinzel, and P. Jurges, Justus Liebigs Ann. Chem., 770, 523 (1974)
10. P. E. Eaton and C. E. Stubbs, J. Am. Chem. Soc., 89, 5722(1967)
11. C. J. Pedersen and A. K. Frensdorf, Angew. Chem., Int. Ed. Engl., 11, 16 (1972)
12. C. J. Pedersen, J. Am. Chem. Soc., 89, 2495, 7017 (1967)
13. G. W. Gokel, D. J. Cram, C. L. Liotta, H. P. Harris, and F. L. Cook, J. Org. Chem., 39, 2445 (1974).
14. A. Nickon and J. L. Lambert, J. Am. Chem. Soc., 88, 1905 (1966)
15. R. Farney, Ph.D. Thesis, University of Illinois, 1974.
16. D. L. Darlrymple, T. L. Kruger, and W. N. White, “The Chemistry of the Ether Linkage”, S. Patai, Ed., Interscience, New York, N.Y., 1967, pp 618-628
17. V. Rautenstrauch, G. Buchi, and H. Wuest, J. Am. Chem. Soc., 96, 2576 (1974)
18. D. W. Slocum and D. I. Sugarmen, Adv. Chem. Ser., 222-247 (1974)
19. D. Hellwinbel and M. Supp, Angew. Chem., Int. Ed. Engl., 13, 270 (1974)
20. H. Gilman and J. W. Marton, Org. React., 8, 258 (1954)
21. J. M. Mallan and R. L. Bebb, Chem. Rev., 69, 693 (1969)
22. D. W. Slocum and B. P. Koonsiuisky, J. Org. Chem., 38, 1675 (1973)
23. R. A. Ellison and F. N. Kotsonis, J. Org. Chem., 38, 4192 (1973)
24. C. D. Broaddus, J. Org. Chem., 35, 10 (1970)
25. R. E. Lundt, G. P. Crowther, and C. R. Hauser, J. Org. Chem., 35, 1288 (1970)
26. H. Watanabe, R. A. Schwartz, C. R. Hauser, J. Lewis, and D. W. Slocum, Can. J. Chem., 67, 1543 (1969)
27. W. E. Parham and Y. A. Sayed, J. Org. Chem., 39, 2051, 2053 (1974)
28. W. H. Puterbaugh and C. R. Hauser, J. Am. Chem. Soc., 85, 2467 (1963)
29. K. C. Wiberg, “Physical Organic Chemistry”, Wiley, New York, N.Y., 1964, p 356
30. G. Knaus and A. I. Meyers, J. Org. Chem., 39, 1192 (1974)
31. F. Westheimer, Chem. Rev., 61, 256 (1961)
32. D. J. Cram, C. A. Kingsbury, and B. Rickborn, J. Am. Chem. Soc., 83, 3688 (1961)
33. A. Streitwieser and H. F. Koch, J. Am. Chem. Soc., 86, 404 (1964)
34. Y. E. Hofman, A. Schriesheim, and R. E. Nicols, Tetrahedron Lett., 1745 (1965).
35. S. C. Watson and J. F. Eastham, J. Organomet. Chem., 9, 165 (1967).
36. C. H. Rehberg and C. H. Fisher, J. Am. Chem. Soc., 66, 1203 (1944).
37. R. Adelman, J. Org. Chem., 14, 1057 (1949).
38. F. E. Clark, S. F. Cox, and E. Mack, J. Am. Chem. Soc., 39, 712 (1939)
39. S. Patai and R. Ikan, J. Org. Chem., 21, 1379 (1956).
40. Monsanto Co., British Patent 969,911; Chem. Abstr., 62, P1603f (1965).
41. C. L. Stevens, M. L. Wernes, and R. C. Freeman, J. Am. Chem. Soc., 75, 3977 (1953).
42. C. F. Woodward, G. T. Borchendt, and R. C. Fuson, J. Am. Chem. Soc., 56, 2103 (1934)
43. W. S. Johnson, A. L. McCloskey, and D. A. Dunnigan, J. Am. Chem. Soc., 72, 514 (1950)
44. W. V. Cohen, U. S. Patent 3,112,256; Chem. Abstr., 60, P15786f (1964).
45. K. Bowden and G. R. Taylor, J. Chem. Soc. B, 149 (1971).
46. H. A. Brunson, U. S. Patent 2,233,513; Chem. Abstr., 35, P36393 (1941).
47. F. Seidel and O. Bezher, Ber., 65, 1566 (1932)
48. L. A. Pavlova and V. Smartseva, J. Org. Chem. USSR, 2, 1686 (1966)