Solid-State and Solution Studies of Lithiated 2-Carbomethoxycyclohexanone Dimethylhydrazone and Lithiated Cyclohexanone Phenylimine

Journal of the American Chemical Society

Volumn 108, Issue 12, 1986, Pages 3415-3422

  Wanat, Robert A ^a   Collum, David B ^a   Duyne, Greg Van ^a   Clardy, Jon ^a   DePue, Randall T ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000014356     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00272a042     Document Type: Article

References (55)

1. Collum, D. B.; Kahne, D.; Gut, S. A.; DePue, R. T.; Mohamadi, F.; Wanat, R. A.; Clardy, J.; Van Duyne, G. J. Am. Chem. Soc. 1985, 106, 4865.
2. Wanat, R. A.; Collum, D. B. J. Am. Chem. Soc. 1985, 107, 2078.
3. Hickmott, P. W. Tetrahedron 1982, 38, 1975.
4. Enders, D. In Current Trends in Organic Synthesis; Nozaki, H., Ed.; Pergamon: New York, 1983.
5. Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517.
6. Fraser, R. R. In Comprehensive Carbanion Chemistry Elsevior: New York, 1980.
7. Huff, B. J. L.; Tuller, F. N.; Caine, D. J. Org. Chem. 1969, 34, 3070.
8. House, H. O.; Umen, M. J. J. Org. Chem. 1973, 38, 1000.
9. Howe, R.; McQuillin, F. J. J. Chem. Soc. 1958, 1194.
10. Kuwajima, I.; Nakamura, E. J. Am. Chem. Soc. 1975, 97, 3257.
11. Djerassi, C.; Osiecki, J.; Eisenbraun, E. J. J. Am. Chem. Soc. 1961, 83, 4433.
12. House, H. O.; Tefertiller, B. A.; Olmstead, H. D. J. Org. Chem. 1968, 33, 935.
13. Kuehne, M. E. J. Org. Chem. 1970, 35, 171.
14. Kuwajima, I.; Nakamura, E.; Shimizu, M. J. Am, Chem. Soc. 1982, 104, 1025.
15. Seebach, D. In Proceedings of the Robert A. Welch Foundation Conferences on Chemical Research XXVII: 1984, p 93.
16. Wakefield, B. J. The Chemistry of Organolithium Compounds; Pergamon Press: New York, 1974; Chapter 1.
17. Wardell, J. J. In Comprehensive Organometallic Chemistry; Stone, F. G. A.; Wilkinson, G.; Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. I.
18. Fraser, R. R. In Comprehensive Carbanion Chemistry; Buncel, E., Durst, T., Eds.; Elsevior: New York, 1980.
19. Cram, D. J. In Fundamentals of Carbanion Chemistry; Academic Press: New York, 1965.
20. Schleyer, P. v. R. Pure Appl. Chem. 1984, 56, 151.
21. Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737.
22. Brown, T. L. Pure Appl. Chem. 1970, 23, 447.
23. Streitwieser, A., Jr. Acc. Chem. Res. 1984, 17, 353.
24. Wehrli, F. J. Magn. Reson. 1978, 30, 193.
25. Seebach, D.; Hassig, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308.
26. Fraenkel, G.; Fraenkel, A. M.; Geckle, M. J.; Schloss, F.J. Am. Chem. Soc. 1979, 101, 4745.
27. Najera, C.; Yus, M.; Hassig, R.; Seebach, D. Helv. Chim. Acta 1984, 67, 1100.
28. Seebach, D.; Gabriel, J.; Hassig, R. Helv. Chim. Acta 1984, 67, 1083.
29. Rajca, A.; Tolbert, L. M. J. Am. Chem. Soc. 1985, 107, 2969.
30. Fraenkel, G.; Henrichs, M.; Hewitt, J. M.; Su, B. M.; Geckle, M. J. J. Am. Chem. Soc. 1980, 102, 3345.
31. Seebach, D.; Bauer von W. Helv. Chim. Acta 1984, 67, 1972.
32. McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805.
33. Arnett, E. M.; Maroldo, S. G.; Schriver, G. W.; Schilling, S. L.; Troughton, E. B. J. Am. Chem. Soc. 1985, 107, 2091.
34. Kimura, B. Y.; Brown, T. L. J. Orzanomet. Chem. 1971, 26, 57.
35. Lappert, M. F.; Slade, M. J.; Singh, A.; Atwood, J. L.; Rogers, R. D.; Shakir, R. J. Am. Chem. Soc. 1983, 105, 302.
36. Engelhardt, L. M.; May, A. S.; Raston, C. L.; White, A. H. J. Chem. Soc., Dalton Trans. 1983, 1671.
37. Seebach, D.; Bauer, W.; Hansen, J.; Laube, T.; Schweizer, W. B.; Dunitz, J. D. J. Chem. Soc., Chem. Commun. 1984, 853.
38. Cetinkaya, B.; Hitchcock, P. B.; Lappert, M. F.; Misra, M. L.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 148.
39. Fjeldberg, T.; Hitchcock, P. B.; Lappert, M. F.; Thorne, A. J. J. Chem. Soc., Chem. Commun. 1984, 823.
40. Power, P. P.; Xiaojie, X. J. Chem. Soc., Chem. Commun. 1984, 358.
41. Barr, B.; Clegg, W.; Mulvey, R. E.; Snaith, R. J. Chem. Soc., Chem. Commun. 1984, 79.
42. J. Chem. Soc., Chem. Commun. 1984, 226.
43. J. Chem. Soc., Chem. Commun. 1984, 469.
44. Laube, T.: Dunitz, J. D.: Seebach D. Helv. Chim. Acta, 1985, 68, 1373.
45. Knorr, R. Weib Low, P.; Rapple, E. Chem. Ber. 1980, 113, 2462.
46. Amirkhalili, S.; Hitchcock, P. B.; Jenkins, A. D.; Nyathi, J. Z.; Smith, J. D. J. Chem. Soc., Dalton Trans. 1981, 377 and references cited therein.
47. Colgan, D.; Papasergio, R. I.; Raston, C. L.; White, A. H. J. Chem. Soc., Chem. Commun. 1984, 1708.
48. Fraser, R. R.; Banville, J.; Dhawan, K. L. J. Am. Chem. Soc. 1978, 100, 7999 and references cited therein.
49. Fraser, R. R.; Chuaqui-Offermanns, N.; Houk, K. N.; Rondan, N. G. J. Organomet. Chem. 1981, 206, 131.
50. Fraser, R. R.; Chuaqui-Offermanns, N. Can. J. Chem. 1981, 59, 3007.
51. Lee, J. Y.; Lynch, T. J.; Mao, D. T.; Bergbreiter, D. E.; Newcomb, M. J. Am. Chem. Soc. 1981, 103, 6215.
52. Houk, K. N.; Strozier, R. W.; Rondan, N. G.; Fraser, R. R.; Chuaqui-Offermanns, N. J. Am. Chem. Soc. 1980, 102, 1427 and references cited therein.
53. Davenport, K. G.; Eichenauer, H.; Enders, D.; Newcomb, M.; Bergbreiter, D. E. J. Am. Chem. Soc. 1979, 101, 5654.
54. Amonoo-Neizer, E. H.; Shaw, R. A.; Skovlin, D. O.; Smith, B. C. Inorg. Synth. 1966, 8, 20.
55. Wanat, R. A. Ph.D. Dissertation, Cornell University, Ithaca, New York, in press.