A Theoretical Study of Proton Transfer in Lithium Carbonyl and Lithium Enolate Complexes

Journal of the American Chemical Society

Volumn 109, Issue 2, 1987, Pages 559-565

  McKee, Michael L ^a  

^a AUBURN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845283487     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00236a039     Document Type: Article

References (42)

1. Wakefield, B. J. in Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon; New York, 1982; Vol. 7, pp 1–110.
2. Wakefield, B. J. The Chemistry of Organolithium Compounds; Per-gamon: Oxford. 1974.
3. Baigrie, L. M.; Seiklay, H. R.; Tidwell, T. T. J. Am. Chem. Soc. 1985, 107, 5391–5396.
4. Beak, P.; Kempf, D. J.; Wilson, K. D. J. Am. Chem. Soc. 1985, 107, 4745–4756. (b) Beak, P.; Hunter, J. E.; Jun, Y. M. J. Am. Chem. Soc. 1983, 105, 6350–6351.
5. House, H. O.; Czuba, L. J.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1969, 34, 2324. (b) House, H. O.; Trost, B. M. J. Org. Chem. 1965, 30, 1341.
6. D’Angelo, J. Tetrahedron 1976, 32, 2979–2990. (b) Jackman, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737–2769.
7. Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868–2877. (b) Corey, E. J.; Gross, A. W. Tetrahedron Lett. 1984, 25, 495–498.
8. Narula, A. S. Tetrahedron Lett. 1981, 22, 4119–4122.
9. Moreland, D. W.; Dauben, W. G. J. Am. Chem. Soc. 1985, 107, 2264–2273.
10. Meyers, A. I. Aldrichimica Acta 1985, 18, 59–68 and references cited therein. (b) Meyers, A. I. Pure Appl. Chem. 1979, 51, 1255–1268.
11. Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066. (b) Evans, D. A.; Nelson. J. V.: Vogel. E. ; Taber. T. R. J. Am. Chem. Soc. 1981. 103. 3099.
12. Shirai, R.; Tanaka, M.; Koga, K. J. Am. Chem. Soc. 1986, 108, 543–545.
13. Stork, G.; Shiner, C. S.; Cheng, C. W. ; Polt, R.L. J. Am. Chem. Soc. 1986, 108, 304–305.
14. Fataftah, Z. A.; Kopka, I. E.; Rathke, M. W. J. Am. Chem. Soc. 1980. 102, 3959–3960.
15. Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y. D. ; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, J. Science (Washington, D. C.) 1986, 231, 1108–1117.
16. Morrison, J. D.; Mosher, H. S. Asymmetric Organic Reactions; American Chemical Society: Washington, DC, 1976. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1984; Vol. 2 and 3. Morrison, J. D.; Mosher, H. S. Science (Washington, D. C.) 1983, 221, 1013.
17. McKee, M. L. J. Am. Chem. Soc. 1985, 107, 7284–7290.
18. McKee, M. L. J. Am. Chem. Soc. 1985, 107, 859–864.
19. Boche, G.; Wagner, H. U. J. Chem. Soc., Chem. Commun. 1984, 1591–1592.
20. Schleyer, P. V. R. Pure Appl. Chem. 1984, 56, 151–162, (b) Schleyer, P. V. R. Pure Appl. Chem. 1983, 55, 355–362. (c) Sapse, A. M. ; Kaufmann, E.; Schleyer, P. V. R.; Gleiter, R. Inorg. Chem. 1984, 23, 1569–1574. (d) Wilhelm, D.; Clark, T.; Schleyer, P. V. R. J. Chem. Soc. Chem. Commun. 1983, 211–214. (e) Jemmis, E. D.; Chandrasekhar, J.; Wurthwein, E. U. ; Schleyer, P. V. R. J. Am. Chem. Soc. 1982, 104, 4275–4276. (f) Schleyer, P. V. R.; Kos, A. J.; Kaufmann, E. J. Am. Chem. Soc. 1983, 105, 7617–7623. (g) Boche, G.; Decher, G.; Etzrodt, H.; Dietrich, H.; Mahdi, W.; Kos, A. J.; Schleyer, P. V. R. J. Chem. Soc., Chem. Commun. 1984, 1493–1494. (h) Kos, A. J.; Clark, T.; Schleyer, P. V. R. Angew. Chem., Int. Ed. Engl. 1984, 23, 620–621. (i) Hagopian, R. A.; Therien, M. J.; Murdoch, J. R. J. Am. Chem. Soc. 1984, 106, 5753–5754.
21. References to basis sets used are collected here. The program package Gaussian 82 Was used throughout: Binkley, J. S.; Frisch, M.; Raghavachari, K.; Fluder, E.; Seeger, R.; Pople, J. A., Carnegie-Mellon University. 3-21G basis; Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939. 3-21+G basis: Clark, T.; Chandrasekhar, J.; Spitznagel, G.; Schleyer, P. V. R. J. Comput. Chem. 1983, 4, 294.
22. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4899–4907, 4907–4917. (b) Lithium parametrization: Thiel, W.; Clark, T., unpublished results.
23. Bachrach, S. M.; Streitwieser, A. J. Am. Chem. Soc. 1986, 108, 3946–3951.
24. Kaufmann, E.; Tidor, B.; Schleyer, P. V. R. J. Comp. Chem. 1986, 7, 334–344.
25. Kaneti, J.; Schleyer, P. V. R.; Clark, T.; Kos, A. J.; Spitznagel, G. W.; Andrade, J. G.; Moffat, J. B. J. Am. Chem. Soc. 1986, 108, 1481–1492.
26. Bays, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
27. Carsky, P.; Urban, M. Ab Initio Calculations; Lecture Notes in Chemistry; Springer-Verlag: Heidelberg, 1980; Vol. 16.
28. Wurthwein, E. U. ; Sen, K. D.; Pople, J. A.; Schleyer, P. V. R. Inorg. Chem. 1983, 22, 496–503.
29. Clark, T.; Chandrasekhar, J.; Spitznagel, G.; Schleyer, P. V. R. J. Comput. Chem. 1983, 4, 294–301.
30. Waterman, K. C.; Streitwieser, A. J. Am. Chem. Soc. 1984, 106, 3138–3140.
31. Bachrach, S. M.; Streitwieser, A. J. Am. Chem. Soc. 1984, 106, 2283–2287.
32. For a recent MNDO study of solvation effects in lithium complexes, see: Kaneti, J.; Schleyer, P. V. R.; Clark, T.; Kos, A. J.; Spitznagel, G. W.; Andrade, J. G.; Moffat, J. B.; J. Am. Chem. Soc. 1986, 108, 1481–1492.
33. Kaufmann, E.; Schleyer, P. V. R.; Houk, K. N.; Wu, Y. D. J. Am. Chem. Soc. 1985, 107, 5560–5562.
34. Del Bene, J. E.; Frisch, M. J.; Raghavachari, K.; Pople, J. A.; Schleyer, P. V. R. J. Phys. Chem. 1983, 87, 73–78.
35. Schleyer, P. V. R.; Clark, T.; Kos, A. J.; Spitznagel, G. W.; Rohde, C.; Arad, D.; Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1984, 106, 6467–6475 and references cited therein.
36. 87, 181–196. (c) Amstutz, R.; Dunitz, J. D.; Laube, T.; Schweizer, W. B.; Seebach, D. Chem. Ber. 1986, 119, 434–443.
37. Seebach, D.; Amstutz, R.; Dunitz, J. D. Helv. Chim. Acta 1981, 64, 2622–2626.
38. Amstutz, R.; Schweizer, W. B.; Seebach, D.; Dunitz, J. D. Helv. Chim. Acta 1981, 64. 2617–2621.
39. Williard, P. G.; Carpenter, G. B. J. Am. Chem. Soc. 1986, 108, 462–468.
40. Laube, T.; Dunitz, J. D.; Seebach, D. Helv. Chim. Acta. 1985, 68, 1373–1393.
41. Creger, P. L. J. Am. Chem. Soc. 1970, 92, 1396–1397. (b) Pfeffer, P. E.; Silbert, L. S.; Chirinko, J. M. J. Org. Chem. 1972, 37, 451. (c) Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390–5398. (d) Aebi, J. D.; Seebach, D. Helv. Chim. Acta 1985, 68, 1507–1518. (e) Strazewski, P.; Tamm, C. Helv. Chim. Acta 1986, 69, 1041–1051.
42. For a CNDO/2 study of this reaction, see: Zakova, M.; Leska, J. Collect. Czech. Chem. Commun, 1983, 48, 433–438.