On the mechanism of lithiation of hydric aromatics: Direct NMR evidence for short H-Li contacts in mixed aggregates

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5194-5195

  Saá, José M ^a   Martorell, Gabriel ^a   Frontera, Antonio ^a  

^a UNIVERSITAT DE LES ILLES BALEARS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000930317     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960570a     Document Type: Article

References (35)

1. (a) Wakefield, B. J. Chemistry of Organolithium Compounds; Pergamon: Oxford, 1974.
2. (b) Gschwend H. W.; Rodriguez, H. R. Org. React. 1979, 26, 1.
3. (c) Klumpp, G. W. Rec. Trav. Chim. Pays-Bas 1986, 105, 1.
4. (d) Snieckus, V. Chem. Rev. 1990, 90, 879.
5. Roberts, J. D.; Curtin, D. Y. J. Am. Chem. Soc. 1946, 68, 1658.
6. (a) van Eikema Homes, N. J. R.; Schleyer, P. v. R. Tetrahedron 1994, 50, 5903 and references cited therein.
7. Resek, J. E.; Beak, P. J. Am. Chem. Soc. 1994, 116, 405.
8. Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356.
9. Remote metalations: (a) Fu, J.-m.; Zhao, B.-p.; Sharp, M. J.; Snieckus, V. J. Org. Chem. 1991, 56, 1683. (b) Coll, G.; Morey, J.; Costa, A.; Saá J. M. J. Org. Chem. 1988, 53, 5345. (c) Bashir-Hashemi, A.; Arduengo, A. J. Chem. Abstr. 1981, 100, 103074q. See also ref 14.
10. Remote metalations: (a) Fu, J.-m.; Zhao, B.-p.; Sharp, M. J.; Snieckus, V. J. Org. Chem. 1991, 56, 1683. (b) Coll, G.; Morey, J.; Costa, A.; Saá J. M. J. Org. Chem. 1988, 53, 5345. (c) Bashir-Hashemi, A.; Arduengo, A. J. Chem. Abstr. 1981, 100, 103074q. See also ref 14.
11. Remote metalations: (a) Fu, J.-m.; Zhao, B.-p.; Sharp, M. J.; Snieckus, V. J. Org. Chem. 1991, 56, 1683. (b) Coll, G.; Morey, J.; Costa, A.; Saá J. M. J. Org. Chem. 1988, 53, 5345. (c) Bashir-Hashemi, A.; Arduengo, A. J. Chem. Abstr. 1981, 100, 103074q. See also ref 14.
12. Hay, D.; Song, Z.; Smith, S. G.; Beak, P. J. Am. Chem. Soc. 1988, 110, 8145 and references cited therein. See also ref 5.
13. (a) Meyers, A. I.; Fuentes, L. M.; Reiker, W. F. J. Am. Chem. Soc. 1983, 105, 2082.
14. (b) Meyers, A. I.; Dickman, D. A. J. Am. Chem. Soc. 1987, 109, 1263.
15. (c) Warmus, J. S.; Rodkin, M. A.; Barkley, R.; Meyers, A. I. J. Chem. Soc., Chem. Commun. 1993, 1357.
16. Bauer, W.; Schleyer, P.v.R. J. Am. Chem. Soc. 1989, 111, 7191 and references therein.
17. Suñer, G. A.; Deyá, P. M.; Saá, J. M. J. Am. Chem. Soc. 1990, 112, 1467. See also ref 14.
18. Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395.
19. Bauer, W.; Clark, T.; Schleyer, P. v. R. J. Am. Chem. Soc. 1987, 109, 970 and references cited therein.
20. Saá, J. M.; Morey, J.; Frontera, A.; Deyá, P. M. J. Am. Chem. Soc. 1995, 117, 1105.
21. Caubère, P. Chem. Rev. 1993, 93, 2317.
22. See: (a) Bauer, W.; Schleyer, P. v. R. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press, Inc.: 1992; Vol. 1.
23. Solutions containing 1:1 (A), 2:1 (B), 3:1 (C), 4:1 (D), and 8:1 (E) n-BuLi:1-naphthol ratios were prepared by adding 1-naphthol (1 mmol) in dry TMEDA (1 mL) to the appropriate amount of nBuLi in TMEDA, at -20 to 0 °C, under argon. n-BuLi in TMEDA was prepared from commercial 2.5M n-BuLi by removing the solvent with dry argon and the residue dissolved in 1 mL of TMEDA. Solvent suppression was achieved in all NMR spectra, except HOESY.
24. Supporting information available.
25. Jackman, L. M.; Scarmoutzos, L. M.; De Brosse, C. W. J. Am. Chem. Soc. 1987, 109, 5355 and references cited therein.
26. 19 depends on the uncertainties regarding the anisotropic rotational diffusion. QSC values for 1 and 3(111 and 135 kHz, respectively) lie close to the ideal 120 kHz.
27. C can be assumed to be ≪1/ω. See: Neuhaus, D.; Williamson, M. P. The Nuclear Overhauser Effect in Structural and Conformational Analysis; VCH: New York, 1989.
28. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H.-R. J. Am. Chem. Soc. 1985, 107, 1810. Bates, T. F.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109. Williard P. G.; Hintze, M. J. J. Am. Chem. Soc. 1990, 112, 8062. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Hanawalt, E. M.; Richey, H. G. Jr. J. Am. Chem. Soc. 1990, 112, 4893. Palmas, P.; Tekeley, P.; Jamart-Gregoire, B.; Caubère, P.; Canet, D. J. Am. Chem. Soc. 1994, 116, 11604. Harder, S.; Lutz, M.; Streitwieser, A. J. Am. Chem. Soc. 1995, 117, 2361. Collum, D. B. Acc. Chem. Res. 1993, 26, 227. See also ref 19.
29. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H.-R. J. Am. Chem. Soc. 1985, 107, 1810. Bates, T. F.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109. Williard P. G.; Hintze, M. J. J. Am. Chem. Soc. 1990, 112, 8062. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Hanawalt, E. M.; Richey, H. G. Jr. J. Am. Chem. Soc. 1990, 112, 4893. Palmas, P.; Tekeley, P.; Jamart-Gregoire, B.; Caubère, P.; Canet, D. J. Am. Chem. Soc. 1994, 116, 11604. Harder, S.; Lutz, M.; Streitwieser, A. J. Am. Chem. Soc. 1995, 117, 2361. Collum, D. B. Acc. Chem. Res. 1993, 26, 227. See also ref 19.
30. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H.-R. J. Am. Chem. Soc. 1985, 107, 1810. Bates, T. F.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109. Williard P. G.; Hintze, M. J. J. Am. Chem. Soc. 1990, 112, 8062. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Hanawalt, E. M.; Richey, H. G. Jr. J. Am. Chem. Soc. 1990, 112, 4893. Palmas, P.; Tekeley, P.; Jamart-Gregoire, B.; Caubère, P.; Canet, D. J. Am. Chem. Soc. 1994, 116, 11604. Harder, S.; Lutz, M.; Streitwieser, A. J. Am. Chem. Soc. 1995, 117, 2361. Collum, D. B. Acc. Chem. Res. 1993, 26, 227. See also ref 19.
31. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H.-R. J. Am. Chem. Soc. 1985, 107, 1810. Bates, T. F.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109. Williard P. G.; Hintze, M. J. J. Am. Chem. Soc. 1990, 112, 8062. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Hanawalt, E. M.; Richey, H. G. Jr. J. Am. Chem. Soc. 1990, 112, 4893. Palmas, P.; Tekeley, P.; Jamart-Gregoire, B.; Caubère, P.; Canet, D. J. Am. Chem. Soc. 1994, 116, 11604. Harder, S.; Lutz, M.; Streitwieser, A. J. Am. Chem. Soc. 1995, 117, 2361. Collum, D. B. Acc. Chem. Res. 1993, 26, 227. See also ref 19.
32. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H.-R. J. Am. Chem. Soc. 1985, 107, 1810. Bates, T. F.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109. Williard P. G.; Hintze, M. J. J. Am. Chem. Soc. 1990, 112, 8062. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Hanawalt, E. M.; Richey, H. G. Jr. J. Am. Chem. Soc. 1990, 112, 4893. Palmas, P.; Tekeley, P.; Jamart-Gregoire, B.; Caubère, P.; Canet, D. J. Am. Chem. Soc. 1994, 116, 11604. Harder, S.; Lutz, M.; Streitwieser, A. J. Am. Chem. Soc. 1995, 117, 2361. Collum, D. B. Acc. Chem. Res. 1993, 26, 227. See also ref 19.
33. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H.-R. J. Am. Chem. Soc. 1985, 107, 1810. Bates, T. F.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109. Williard P. G.; Hintze, M. J. J. Am. Chem. Soc. 1990, 112, 8062. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Hanawalt, E. M.; Richey, H. G. Jr. J. Am. Chem. Soc. 1990, 112, 4893. Palmas, P.; Tekeley, P.; Jamart-Gregoire, B.; Caubère, P.; Canet, D. J. Am. Chem. Soc. 1994, 116, 11604. Harder, S.; Lutz, M.; Streitwieser, A. J. Am. Chem. Soc. 1995, 117, 2361. Collum, D. B. Acc. Chem. Res. 1993, 26, 227. See also ref 19.
34. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H.-R. J. Am. Chem. Soc. 1985, 107, 1810. Bates, T. F.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109. Williard P. G.; Hintze, M. J. J. Am. Chem. Soc. 1990, 112, 8062. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Hanawalt, E. M.; Richey, H. G. Jr. J. Am. Chem. Soc. 1990, 112, 4893. Palmas, P.; Tekeley, P.; Jamart-Gregoire, B.; Caubère, P.; Canet, D. J. Am. Chem. Soc. 1994, 116, 11604. Harder, S.; Lutz, M.; Streitwieser, A. J. Am. Chem. Soc. 1995, 117, 2361. Collum, D. B. Acc. Chem. Res. 1993, 26, 227. See also ref 19.
35. McGarrity, J. F.; Ogle, C. A.; Brich, Z.; Loosli, H.-R. J. Am. Chem. Soc. 1985, 107, 1810. Bates, T. F.; Thomas, R. D. J. Am. Chem. Soc. 1988, 110, 5109. Williard P. G.; Hintze, M. J. J. Am. Chem. Soc. 1990, 112, 8062. Marsch, M.; Harms, K.; Lochmann, L.; Boche, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 308. Hanawalt, E. M.; Richey, H. G. Jr. J. Am. Chem. Soc. 1990, 112, 4893. Palmas, P.; Tekeley, P.; Jamart-Gregoire, B.; Caubère, P.; Canet, D. J. Am. Chem. Soc. 1994, 116, 11604. Harder, S.; Lutz, M.; Streitwieser, A. J. Am. Chem. Soc. 1995, 117, 2361. Collum, D. B. Acc. Chem. Res. 1993, 26, 227. See also ref 19.