Effect of solvent on the lithium-bromine exchange of aryl bromides: Reactions of n-butyllithium and tert-butyllithium with 1-bromo-4-tert- butylbenzene at 0 °C

Journal of Organic Chemistry

Volumn 71, Issue 7, 2006, Pages 2825-2828

  Bailey, William F ^a   Luderer, Mark R ^a   Jordan, Kevin P ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; EXCHANGE REACTION; SOLVENT SYSTEMS;

BENZENE; BROMINE COMPOUNDS; HEPTANE; HYDROCARBONS; LITHIUM; SOLVENTS;

AROMATIC COMPOUNDS;

(4 TERT BUTYLPHENYL)LITHIUM; 1 BROMO 4 TERT BUTYLBENZENE; BROMINE; ETHER; HEPTANE; HYDROCARBON; LITHIUM; N BUTYLLITHIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SOLVENT; TERT BUTYLLITHIUM; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CAPILLARY GAS CHROMATOGRAPHY; CHEMICAL COMPOSITION; CHEMICAL REACTION; CHEMICAL STRUCTURE; LITHIUM BROMIDE EXCHANGE REACTION; LOW TEMPERATURE; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

BENZENE DERIVATIVES; ETHERS; HEPTANES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; TEMPERATURE;

EID: 33645524145     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060026u     Document Type: Article

References (34)

1. Bailey, W. F.; Brubaker, J. D.; Jordan, K. P. J. Organomet. Chem. 2003, 681, 210.
2. (a) Wittig, G.; Pockels, U.; Droge, H. Chem. Ber. 1938, 71, 1903.
3. (b) Gilman, H.; Langham, W.; Jacoby, A. L. J. Am. Chem. Soc. 1939, 61, 106.
4. (c) It is of some historical interest to note that the lithium-bromine exchange was observed by Marvel and co-workers at least a decade before these reports: treatment of m-bromotoluene with n-BuLi at room temperature for 4 d in petroleum ether gave an 87% yield of toluene after quench with water, but the implications of this observation were not recognized at the time. See: Marvel, C. S.; Hager, F. D.; Coffman, D. D. J. Am. Chem. Soc. 1927, 49, 2323.
5. (a) Jones, R. G.; Gilman, H. Chem. Rev. 1954, 54, 835.
6. (b) Gilman, H.; Jones, R. G. Org. React. (NY) 1951, 6, 339.
7. (c) Schölkopf, U. In Methoden der Organischen Chemie; Georg Thieme: Stuttgart, 1970; Vol. 13/1.
8. (d) Wakefield, B. J. The Chemistry of Organolithium Compounds; Pergamon Press: New York, 1974.
9. (e) Wardell, J. L. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: New York, 1982; Vol. 1, p 43.
10. (f) Wakefield, B. J. Organolithium Methods; Pergamon Press: New York, 1988.
11. (g) Bailey, W. F.; Patricia, J. J. J. Organomet. Chem. 1988, 352, 1.
12. (h) Schlosser, M. In Organometallics in Synthesis: A Manual; Schlosser, M., Ed.; Wiley: New York, 2002; pp 101-137.
13. (i) Sapse, A. M.; Schleyer, P. v. R. Lithium Chemistry: A Theoretical and Experimental Overview; Wiley: New York, 1995.
14. (j) Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon Press: New York, 2002; pp 111-135.
15. Applequist, D. E.; O'Brien, D. F. J. Am. Chem. Soc. 1963, 85, 743.
16. Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967.
17. No attempt was made to quantitate the amounts, if any, of butane, 1-butene, 1-bromobutane, or octane that may have been produced from extraneous reactions of n-BuLi.
18. Fields, E. K. J. Org. Chem. 1978, 25, 4705.
19. Brown, T. L. Acc. Chem. Res. 1968, 1, 23.
20. West, P.; Waack, R. J. Am. Chem. Soc. 1967, 89, 4395.
21. (a) McGarrity, J. F.; Ogle, C. A. J. Am. Chem. Soc. 1985, 107, 1805.
22. (b) Bauer, W.; Winchester, W. R.; Schleyer, P. v. R. Organometallics 1987, 6, 2371.
23. Reich, H. J.; Green, D. P.; Medina, M. A.; Goldenberg, W. S.; Gudmundsson, B. O.; Dykstra, R. R.; Phillips, N. H. J. Am. Chem. Soc. 1998, 120, 7201 and references therein.
24. Merrill, R. E.; Negishi, E. J. Org. Chem. 1974, 39, 3452.
25. (a) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
26. (b) Seebach, D.; Neumann, H. Chem. Ber. 1974, 107, 847.
27. Okada, T.; Karaki, I.; Mataga, N. J. Am. Chem. Soc. 1982, 104, 7191.
28. Thomas, R. D.; Clarke, M. T.; Jensen, R. M.; Young, T. C. Organometallics 1985, 5, 1851.
29. In light of the fairly rapid consumption of t-BuLi by proton abstraction from various ethers at 0 °C, the exchange reaction between 1 and t-BuLi in solvent containing more than 10% by volume of an ether was not investigated. The half-life of t-BuLi in various solvents has been reported; see: Stanetty, P.; Mihovilovic, M. J. Org. Chem. 1997, 62, 1514.
30. Bates, T. F.; Clarke, M. T.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109.
31. Bauer, W.; Winchester, W. R.; Schleyer, P.v. R. Organometallics 1987, 6, 2371.
32. Snieckus, V. Chem Rev. 1990, 90, 879 and references therein.
33. Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165.
34. Hennion, G. F.; Auspos, L. A. J. Am. Chem. Soc. 1943, 65, 1943.