Interconversion of contact and separated ion pairs in silyl- and arylthio-substituted alkyllithium reagents

Organic Letters

Volumn 8, Issue 18, 2006, Pages 4003-4006

  Reich, Hans J ^a   Sikorski, William H ^a   Thompson, Jennifer L ^a   Sanders, Aaron W ^a   Jones, Amanda C ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748945005     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061489p     Document Type: Article

References (57)

1. (a) Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 277-297.
2. (b) Schade, S.; Boche, G. J. Organomet. Chem. 1998, 550, 359-379.
3. Schade, S.; Boche, G. J. Organomet. Chem. 1998, 550, 381-395.
4. Günther, H.; Moskau, D.; Bast, P.; Schmalz, D. Angew. Chem., Int. Ed. Engl. 1987, 26, 1212-1220.
5. Klumpp, G. W. Rec. Trav. Chim. Pays-Bas 1986, 105, 1-21.
6. (a) Hogen-Esch, T. E. Adv. Phys. Org. Chem. 1977, 15, 153-266.
7. (b) Chang, C. J.; Kiesel, R. F.; Hogen-Esch, T. E. J. Am. Chem. Soc. 1973, 95, 8446-8448.
8. (a) Schleyer, P. v. R. Pure Appl. Chem. 1984, 56, 151-162.
9. Setzer, W. N.; Schleyer, P. v. R. Adv. Organomet. Chem. 1985, 24, 353-451.
10. (b) Bauer, W.; Winchester, W. R.; Schleyer, P. v. R. Organometallics 1987, 6, 2371-2379.
11. (c) Winchester, W. R.; Bauer, W.; Schleyer, P. v. R. J. Chem. Soc., Chem. Commun. 1987, 177-179.
12. (a) Reich, H. J.; Borst, J. P.; Dykstra, R. R.; Green, D. P. J. Am. Chem. Soc. 1993, 115, 8728-8741.
13. (b) Reich, H. J.; Sanders, A. W.; Fiedler, A. T.; Bevan, M. J. J. Am. Chem. Soc. 2002, 124, 13386-13387.
14. (c) Reich, H. J.; Sikorski, W. H. J. Org. Chem. 1999, 64, 14-15.
15. Sikorski, W. H.; Reich, H. J. J. Am. Chem. Soc. 2001, 123, 6527-6535.
16. (d) Reich, H. J.; Holladay, J. E.; Mason, J. D.; Sikorski, W. H. J. Am. Chem. Soc. 1995, 117, 12137-12150.
17. (e) Reich, H. J.; Dykstra, R. R. J. Am. Chem. Soc. 1993, 115, 7041-7042.
18. (f) Reich, H. J.; Thompson, J. L. Org. Lett. 2000, 2, 783-786.
19. (g) The DNMR simulations were performed with an updated version of WINDNMR (http://www.chem.wisc.edu/areas/reich/plt/windn-mr.htm). Reich, H. J. J. Chem. Educ.: Software, Ser. D 1996, 3, No. 2.
20. 3CH: Sikorski, W. H.; Sanders, A. W.; Reich, H. J. Magn. Reson. Chem. 1998, 36, S118-S124.
21. Schmitt, B. J.; Schultz, G. V. Eur. Polym. J. 1975, 11, 119-130.
22. Ellington, J. C., Jr.; Arnett, E. M. J. Am. Chem. Soc. 1988, 110, 7778-7785.
23. Krom, J. A.; Streitwieser, A. J. Am. Chem. Soc. 1992, 114, 8747-8748.
24. Panek, E. J.; Rodgers, T. J. J. Am. Chem. Soc. 1974, 96, 6921-6928.
25. Canepa, C.; Prandi, C.; Venturello, P. Tetrahedron 1994, 50, 8161-68.
26. Cohen, T.; Abraham, W. D.; Myers, M. J. Am. Chem. Soc. 1987, 109, 7923-7924.
27. Juaristi, E.; Cruz-Sánchez, J. S.; Ramos-Morales, F. R. J. Org. Chem. 1984, 49, 4912-4917.
28. (a) Eaborn, C.; Hitchcock, P. B.; Smith, J. D.; Sullivan, A. C. J. Chem. Soc., Chem. Commun. 1983, 827-828.
29. Buttrus, N. H.; Eaborn, C. Hitchcock, P. B.; Smith, J. D.; Stamper, J. G.; Sullivan, A. C. J. Chem. Soc., Chem. Commun. 1986, 969-970.
30. (b) Avent, A. G.; Eaborn, C. Hitchcock, P. B.; Lawless, G. A.; Lickiss, P. D.; Mallien, M.; Smith, J. D. Webb, A. D.; Wrackmeyer, B. J. Chem. Soc., Dalton Trans. 1993, 3259-3264.
31. (c) For example, the compound can be steam distilled and does not react with either bromine or boiling concentrated hydrochloric acid. Eaborn, C.; Retta, N.; Smith, J. D. J. Organomet. Chem. 1980, 190, 101-106.
32. Hiller, W.; Layh, M.; Uhl, W. Angew. Chem., Int. Ed. Engl. 1991, 30, 324-326.
33. (a) Seebach, D.; Meyer, N.; Beck, A. K. Liebigs Ann. Chem. 1977, 846-858.
34. (b) Seebach, D.; Hässig, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308-337.
35. 5b For an explanation, see: Bacon, J.; Gillespie, R. J.; Quail, J. W. Can. J. Chem. 1963, 41, 3063-3069.
36. 6a solvated species, where the SIP and CIP have different levels of crypt/HMPA solvation. Such strong ligands for lithium have relatively slow ligand exchange rates, so distinct solvates can be readily observed on the NMR time scale.
37. Cahen, Y. M.; Dye, J. L.; Popov, A. I. J. Phys. Chem. 1975, 79, 1289-1292.
38. Cahen, Y. M.; Dye, J. L.; Popov, A. I. J. Phys. Chem. 1975, 79, 1292-1295.
39. Shamsipur, M.; Karkhaneei, E.; Afkhami, A. Polyhedron 1998, 17, 3809-3815.
40. Gais, H.-J.; Vollhardt, J.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1988, 27, 1092-1094.
41. Saunders, M.; Telkowski, L.; Kates, M. R. J. Am. Chem. Soc. 1977, 99, 8070-8071.
42. Dziembowska, T.; Hansen, P. E.; Rozwadowski, Z. Prog. NMR Spectrosc. 2004, 45, 1-29.
43. Siehl, H.-U. Adv. Phys. Org. Chem. 1987, 23, 63-163.
44. Günther, H.; Aydin, R. J. Am. Chem. Soc. 1981, 103, 1301-1303.
45. Schlosser, M.; Stähle, M. Angew. Chem., Int. Ed. 1980, 19, 487-489.
46. Fraenkel, G.; Chow, A.; Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 1382-1386.
47. (a) Jonsäll, G.; Ahlberg, P. J. Chem. Soc., Perkin Trans. 2 1987, 461-467.
48. (b) Ahlberg, P.; Davidsson, Ö.; Löwendahl, M.; Hilmersson, G.; Karlsson, A.; Håkansson, M. J. Am. Chem. Soc. 1997, 119, 1745-1750.
49. Christl, M.; Leininger, H.; Brückner, D. J. Am. Chem. Soc. 1983, 105, 4843-4844.
50. Interconversion of SIP/CIP of lithium naphthalide in THF-ether is ΔG‡ = 3.5 kcal/mol at -50 EC. Hirota, N.; Carraway, R.; Schook, W. J. Am. Chem. Soc. 1968, 90, 3611-3618.
51. 26b mechanisms.
52. Puchta, R.; Galle, M.; van Eikema Hommes, N.; Pasgreta, E.; van Eldik, R. Inorg. Chem. 2004, 43, 8227-8229.
53. Spongberg, D.; Rey, R.; Hynes, J. T.; Hermansson, K. J. Phys. Chem. B 2003, 107, 4470-4477.
54. (a) Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1996, 118, 2217-2225.
55. (b) Lucht, B. L.; Collum, D. B. J. Am. Chem. Soc. 1995, 117, 9863-9874.
56. Hilmersson, G.; Davidsson, Ö. J. Org. Chem. 1995, 60, 7660-7669.
57. 10a