Reaction of organolithium compounds with alkali metal alkoxides - A route to superbases

European Journal of Inorganic Chemistry

Volumn , Issue 6, 2000, Pages 1115-1126

  Lochmann, Lubomír ^a,b,c  

^a INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Czech Republic)

^b CZECH TECHNICAL UNIVERSITY IN PRAGUE   (Czech Republic)

^c Department of Obstetrics Gynecology   (United States)

Author keywords

Alkali metal alkoxides; Alkali metals; Metal exchange; Metallation; Organolithium compounds

Indexed keywords

ALKALI METALS; KETONES; LITHIUM COMPOUNDS; ORGANOMETALLICS;

ALKALI METAL ALKOXIDE; HEAVY ALKALI METALS; LITHIUM ALKOXIDES; LITHIUM ENOLATES; METAL ALKOXIDES; METAL ORGANIC COMPOUND; METAL-EXCHANGE; METALLATION; ORGANOLITHIUM COMPOUNDS; SUPERBASES;

SUBSTRATES;

ALKALI METAL; ESTER; KETONE; LITHIUM; ORGANOLITHIUM COMPOUND;

CATALYSIS; CATALYST; CHEMICAL REACTION; REVIEW; SYNTHESIS;

EID: 0034088591     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0682(200006)2000:6<1115::AID-EJIC1115>3.3.CO;2-B     Document Type: Review

References (85)

1. C. F. Wofford (to Phillips Petroleum Co.), US Patent 3,294.768; appl. November 14, 1963.
2. H. L. Hsieh, C. F. Wofford, J. Polym. Sci., Part A-I 1969, 7, 449.
3. L. Lochmann, J. Pospíšil, D. Lím, Czech. Pat. 132.254; appl. December 30, 1964; Chem. Abstr. 1970, 73, 25642f.
4. L. Lochmann, J. Pospíšil, D. Lím, Czech. Pat. 132.254; appl. December 30, 1964; Chem. Abstr. 1970, 73, 25642f.
5. J. Báča, L. Lochmann, K. Jůzl, J. Čoupek, D. Lím, Symposium on Macromolecules, Prague, 1965, Preprint No. P 508, submitted June 6, 1965; J. Polym. Sci., Part C 1968, 16, 3865.
6. J. Báča, L. Lochmann, K. Jůzl, J. Čoupek, D. Lím, Symposium on Macromolecules, Prague, 1965, Preprint No. P 508, submitted June 6, 1965; J. Polym. Sci., Part C 1968, 16, 3865.
7. L. Lochmann. J. Pospíšil, D. Lím, Tetrahedron Lett. 1966, 257.
8. L. Lochmann, D. Lím, J. Organomet. Chem. 1971, 28, 153.
9. L. Lochmann, J. Trekoval, Collect. Czech. Chem. Commun. 1988, 53, 76.
10. L. Lochmann, J. Organomet. Chem. 1989, 364, 281.
11. L. Lochmann, J. Organomet. Chem. 1989, 376, 1.
12. H. Andringa, H. D. Verkruijsse, L. Brandsma, L. Lochmann, J. Organomet. Chem. 1990, 393, 307.
13. L. Lochmann, J. Petránek, Tetrahedron Lett. 1991, 32, 1483.
14. M. Schlosser, J. Organomet. Chem. 1967, 8, 9.
15. M. Schlosser, Pure Appl. Chem. 1988, 60, 1627.
16. M. Schlosser, Mod. Synth. Methods 1992, 6, 227.
17. G. Boche, H. Etzrodt, Tetrahedron Lett. 1983, 24, 5477.
18. D. Wilhelm, T. Clark, P. v. R. Schleyer, J. Courtneige, A. G. Davies, J. Organomet. Chem. 1984, 275, C1.
19. D. Wilhelm, T. Clark, P. v. R. Schleyer, J. Chem. Soc., Chem. Commun. 1983, 211.
20. C. Schade, W. Bauer, P. v. R. Schleyer, J. Organomet. Chem. 1985, 295, C25.
21. R. Pi, W. Bauer, B. Brix, C. Schade, P. v. R. Schleyer, J. Organomet. Chem. 1986, 306, C1.
22. L. Brandsma, H. D. Verkruijsse, C. Schade, P. v. R. Schleyer, J. Chem. Soc., Chem. Commun. 1986, 260.
23. B. Gordon III, M. Blumenthal, Polym. Bull. (Berlin) 1985, 14, 69.
24. J. J. Bahl, R. B. Bates, B. Gordon III, J. Org. Chem. 1979, 44, 2290.
25. N. S. Mills, A. R. Rusinko III, J. Org. Chem. 1986, 51, 2567.
26. L. Brandsma, H. D. Verkruijsse, Preparative Polar Organometallic Chemistry, vol. 1, Springer, Berlin, 1987.
27. L. Brandsma, Preparative Polar Organometallic Chemistry, vol. 2, Springer, Berlin, 1990.
28. T. L. Brown, J. A. Ladd, G. M. Newman, J. Organomet. Chem. 1965, 3, 1.
29. M. Y. Darensbourg, B. Y. Kimura, G. E. Hartwell, T. L. Brown, J. Am. Chem. Soc. 1970, 92, 1236.
30. J. F. McGarrity, C. A. Ogle, J. Am. Chem. Soc. 1985, 107, 1805.
31. L. Lochmann, J. Pospíšil, J. Vodňanský, J. Trekoval, D. Lím, Collect. Czech. Chem. Commun. 1965, 30, 2187.
32. G. E. Coates, K. Wade, Organometallic Compounds, vol. I, Methuen, London, 1967.
33. W. N. Setzer, P. v. R. Schleyer, Adv. Organomet. Chem. 1985, 24, 353; cf. also: C. Schade, P. v. R. Schleyer, Adv. Organomet. Chem. 1987, 27, 169.
34. W. N. Setzer, P. v. R. Schleyer, Adv. Organomet. Chem. 1985, 24, 353; cf. also: C. Schade, P. v. R. Schleyer, Adv. Organomet. Chem. 1987, 27, 169.
35. V. Halaška, L. Lochmann, D. Lím, Collect. Czech. Chem. Commun. 1968, 33, 3245.
36. M. Marsch, K. Harms, L. Lochmann, G. Boche, Angew. Chem. 1990, 102, 334; Angew. Chem. Int. Ed. Engl. 1990, 29.
37. M. Marsch, K. Harms, L. Lochmann, G. Boche, Angew. Chem. 1990, 102, 334; Angew. Chem. Int. Ed. Engl. 1990, 29.
38. V. Halaška, L. Lochmann, Collect. Czech. Chem. Commun. 1973, 38, 1780.
39. L. Lochmann, R. Lukáš, Collect. Czech. Chem. Commun. 1972, 37, 569.
40. J. F. McGarrity, C. A. Ogle, Z. Brich, H.-R. Loosli, J. Am. Chem. Soc. 1985, 107, 1810.
41. H. L. Hsieh, J. Polym. Sci. A-1 1970, 8, 533.
42. P. Caubére, Chem. Rev. 1993, 93, 2317.
43. L. Lochmann, J. Trekoval, Czechoslovak Discovery No. 60, Czechoslovak Bureau of Patents and Discoveries, Prague, 1991.
44. L. Lochmann, J. Trekoval, J. Organomet. Chem. 1979, 179, 123.
45. L. Lochmann, J. Trekoval, J. Organomet. Chem. 1987, 326, 1.
46. L. Lochmann, J. Trekoval, J. Organomet. Chem. 1975, 99, 329.
47. L. Lochmann, R. L. De, J. Trekoval, J. Organomet. Chem. 1978, 156, 307.
48. W. Bauer, L. Lochmann, J. Am. Chem. Soc. 1992, 114, 7482.
49. Eur. Patent Appl. 41306; Chem. Abstr. 1981, 96, 123007. Preparation of a heptane solution of 2-ethylhexylsodium was checked in the author's laboratory. Protolysis of this solution gave almost the expected amount of 3-methylheptane.
50. L. Lochmann, J. Čoupek, D. Lím, Collect. Czech. Chem. Commun. 1970, 35, 733.
51. H. F. Ebel, Methoden Org. Chem. (Hauben-Weyl), 1970, vol. XIII/1, p. 388.
52. W. H. Glaze, D. P. Duncan, J. Organomet. Chem. 1975, 99, 11.
53. S. H. Bertz, Ch. P. Gibson, G. Dabbagh, Organometallics 1988, 7, 227.
54. E. Weiss, G. Sauermann, Chem Ber. 1970, 103, 265.
55. E. Weiss, G. Sauermann, J. Organomet. Chem. 1970, 21, 1.
56. E. Weiss, H. Koester, Chem. Ber. 1977, 110, 717.
57. E. Weiss, G. Sauermann, G. Thirase, Chem. Ber. 1983, 116, 741.
58. G. Thirase, E. Weiss, J. Organomet. Chem. 1974, 81, C1.
59. L. Lochmann, unpublished results.
60. L. Lochmann, H. Jakubův, L. Brandsma, Collect. Czech. Chem. Commun. 1993, 58, 1445.
61. L. Lochmann, Collect. Czech. Chem. Commun. 1987, 52, 2710.
62. D. Hoffmann, W. Bauer, F. Hampel, N. J. R. van Eikema Hommes, P. v. R. Schleyer, P. Otto, U. Pieper, D. Stalke, D. S. Wright, R. Snaith, J. Am. Chem. Soc. 1994, 116, 528.
63. D. Bucca, B. Gordon III, Macromolecules 1994, 27, 862.
64. M. Schlosser, S. Strunk, Tetrahedron Lett. 1984, 25, 741.
65. L. Lochmann, M. Fossatelli, L. Brandsma, Recl. Trav. Chim. Pays-Bas 1990, 109, 529.
66. L. Lochmann, J. M. J. Fréchet, Macromolecules 1996, 29, 1767.
67. L. Lochmann, M. Rodová, J. Trekoval, J. Polym. Sci., Polym. Chem. Ed. 1974, 72, 2091.
68. L. Lochmann, D. Doskočilová, J. Trekoval, Collect. Czech. Chem. Commun. 1977, 42, 1355.
69. L. Lochmann, J. Trekoval, Collect. Czech. Chem. Commun. 1986, 51, 1439.
70. B. Gordon III, J. E. Loftus, D. Bucca, Polym. Prepr. 1988, 29(2), 21.
71. I. Yu. Kirchevskaya, A. R. Samotsvetov, N. P. Seredina, N. I. Urazov, V. P. Shatalov, Vysokomol. Soedin., Sci: A 1976, 18, 1844; Chem. Abstr. 1976, 55, 178051o.
72. I. Yu. Kirchevskaya, A. R. Samotsvetov, N. P. Seredina, N. I. Urazov, V. P. Shatalov, Vysokomol. Soedin., Sci: A 1976, 18, 1844; Chem. Abstr. 1976, 55, 178051o.
73. T. C. Cheng, A. F. Halasa, J. Polym. Sci., Polym. Chem. Ed. 1976, 14, 573.
74. M. J. Farral, J. M. J. Fréchet, J. Org. Chem. 1976, 41, 3877.
75. G. Clouet, J. Brossas, Makromol. Chem. 1979, 180, 867.
76. G. J. Beinert, J. G. Zilliox, J. E. Herz, Makromol. Chem. 1993, 194, 3184.
77. L. Lochmann, M. Janata, P. Holler, Z. Tuzar, P. Kratochvil, Macromolecules 1996, 29, 8092.
78. S. Nemes, J. Borbély, J. Borda, T. Kelen, Polym. Bull. (Berlin) 1991, 27, 123.
79. A. F. Halasa, G. B. Mitchell, M. Stayer, D. P. Tate, A. E. Oberster, R. W. Koch, J. Polym. Sci., Polym. Chem. Ed. 1976, 14, 497.
80. L. Lochmann, K. L. Wooley, P. T. Ivanova, J. M. J. Fréchet, J. Am. Chem. Soc. 1993, 115, 7043.
81. J. M. J. Fréchet, L. Lochmann, V. Šmigol, F. Švec, J. Chromatogr. A 1994, 607, 284.
82. M. Janata, L. Lochmann, J. Brus, P. Holler, Z. Tuzar, P. Kratochvil, B. Schmitt, W. Radke, A. H. E. Müller, Macromolecules 1997, 30, 7370.
83. T. Kremer, S. Harder, M. Junge, P. v. R. Schleyer, Organometallics 1996, 15, 585.
84. G. Ghio, G. Tonachini, P. Venturello, Tetrahedron 1996, 52, 7053.
85. S. Harder, A. Streitwieser, Angew. Chem. Int. Ed. Engl. 1993, 32, 1066.