Relative basicities of ortho-, meta-, and para-substituted aryllithiums

Journal of Organic Chemistry

Volumn 74, Issue 1, 2009, Pages 222-229

  Gorecka Kobylinska, Joanna ^a   Schlosser, Manfred ^a  

^a EPFL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL ANIONS; CHEMICAL EQUATIONS; CORRELATION FACTORS; GAS PHASE; IODOARENES; METHOXY; PARA POSITIONS; PROTONATION ENTHALPIES; RELATIVE BASICITIES; TETRAHYDROFURAN; TRIFLUORO METHYLS;

CHEMICAL REACTIONS; CHLORINE; EQUILIBRIUM CONSTANTS; FLUORINE; NEGATIVE IONS; ORGANIC POLYMERS;

ALKALINITY;

LITHIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 58149280404     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8020083     Document Type: Article

References (46)

1. Büker, H. H.; Nibbering, N. M. M.; Espinosa, D.; Mongin, F.; Schlosser, M. Tetrahedron Lett. 1997, 38, 8519-8522.
2. Schlosser, M.; Marzi, E. Chem. Eur. J. 2005, 11, 3449-3454.
3. Schlosser, M.; Marzi, E.; Cottet, F.; Büker, H. H.; Nibbering, N. M. M. Chem. Eur. J. 2001, 7, 3511-3516.
4. Andrade, P. B. M.; Riveras, J. M. J. Mass Spectrom. 1996, 31, 767-770;
5. Chem. Abstr. 1996, 125, 247111.
6. Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, C. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590-2599.
7. Schlosser, M.; Mongin, F.; Porwisiak, J.; Dmowski, W.; Büker, H. H.; Nibbering, N. M. M. Chem. Eur. J. 1998, 7, 1281-1286.
8. Kovačević, B.; Maksić, Z. B.; Primorac, M. Eur. J. Org. Chem. 2003, 3777-3783.
9. Dahlke, G. D.; Kass, S. R. Int. J. Mass Spectrom. Ion Proc. 1992, 117, 633-645.
10. Maggi, R.; Schlosser, M. Tetrahedron Lett. 1999, 40, 8797-8800.
11. Castagnetti, E.; Schlosser, M. Chem. Eur. J. 2002, 8, 799-804.
12. Mongin, F.; Maggi, R.; Schlosser, M. Chimia 1996, 50, 650-652.
13. Marzi, E.; Mongin, F.; Spitaleri, A.; Schlosser, M. Eur. J. Org. Chem. 2001, 2911-2915.
14. Wittig, G.; Pockels, U.; Dröge, H. Ber. Dtsch. Chem. Ges. 1938, 71, 1903-1912.
15. (a) Hubbard, W. N.; Knowlton, J. W.; Huffman, H. M. J. Phys. Chem. 1954, 58, 396-402.
16. (b) Platonov, V. A.; Simulin, Y. N. Zh. Fiz. Khim. 1984, 58, 2682-2686;
17. Russ. J. Phys. Chem. (Engl. Transl.) 1984, 58, 1630-1632;
18. Chem. Abstr. 1985, 102, 33733.
19. Taskinen, E. Struct. Chem. 2000, 11, 293-301;
20. Chem. Abstr. 2000, 134, 41897.
21. Gilman, H.; Jones, R. G. J. Am. Chem. Soc. 1941, 63, 1441-1443.
22. Winkler, H. J. S.; Winkler, H. J. Am. Chem. Soc. 1966, 88, 964-969.
23. Leroux, F.; Jeschke, P.; Schlosser, M. Chem. Rev. 2005, 105, 827-856.
24. Castagnetti, E.; Schlosser, M. Eur. J. Org. Chem. 2001, 691-695.
25. Schlosser, M.; Gorecka, J.; Castagnetti, E. Eur. J. Org. Chem. 2003, 452-462.
26. Gorecka, J.; Leroux, F.; Schlosser, M. Eur. J. Org. Chem. 2004, 64-68.
27. Leroux, F.; Gorecka, J.; Schlosser, M. Synthesis 2004, 326-328.
28. Hyla-Kryspin, I.; Grimme, S.; Büker, H. H.; Nibbering, N. M. M.; Cottet, F.; Schlosser, M. Chem. Eur. J. 2005, 11, 1251-1256.
29. Stratakis, M.; Wang, P. G.; Streitwieser, A. J. Org. Chem. 1996, 61, 3145-3150.
30. Chadwick, S. T.; Rennels, R. A.; Rutherford, J. L.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 8640-8647.
31. Jones, F. N.; Vaulx, R. L.; Hauser, C. R. J. Org. Chem. 1963, 28, 3461-3465.
32. Klein, K. P.; Hauser, C. R. J. Org. Chem. 1967, 32, 1479-1483.
33. Schlosser, M.; Ginanneschi, A.; Leroux, F. Eur. J. Org. Chem. 2006, 2956-2969.
34. Fowell, P. A.; Mortimer, C. T. J. Chem. Soc. 1961, 3793-3796.
35. Holm, T. J. Organomet. Chem. 1974, 77, 27-30.
36. Klumpp, G. W. Recl. Trav. Chim. Pays-Bas 1986, 105, 1-21.
37. Arnett, E. M.; Moe, K. D. J. Am. Chem. Soc. 1991, 113, 7068-7069.
38. van Eikema Hommes, N. J. R.; Schleyer, P. V. R. Angew. Chem. 1992, 104, 768-771;
39. Angew. Chem., Int. Ed. Engl. 1992, 31, 755-758.
40. Woodin, R. L.; Beauchamp, J. L. J. Am. Chem. Soc. 1978, 100, 501-508.
41. Kaufmann, L.; Vitze, H.; Bolte, M.; Lerner, H.-W.; Wagner, M. Organometallics 2007, 26, 1771-1776.
42. Rodgers, M. T.; Armentrout, P. B. Int. J. Mass Spectrom. 2007, 267, 167-182.
43. Schlosser M. In Organometallics in Synthesis: A Manual, 2nd ed.; Schlosser, M., Ed.; Wiley: Chichester, 2002; pp 1-352; spec. 47-49.
44. Masson, E.; Schlosser, M. Eur. J. Org. Chem. 2005, 4401-4405.
45. Leroux, F.; Lefebvre, O.; Schlosser, M. Eur. J. Org. Chem. 2006, 3147-3151.
46. Heiss, C.; Marzi, E.; Mongin, F.; Schlosser, M. Eur. J. Org. Chem. 2007, 669-675.