Organolithium additions to styrene are synthetically viable

Chemical Communications

Volumn , Issue 2, 1996, Pages 187-188

  Wei, Xudong ^a,b   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003162393     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000187     Document Type: Article

References (17)

1. For a recent review of alkene carbometallation (including carbolithiation) see P. Knochel, in Comprehensive Organic Synthesis, Pergamon, Oxford, 1991, vol. 4, ch. 4.4; see also B. J. Wakefield, The Chemistry of Organolithium Compounds, Pergamon, Oxford, 1974, section 7.1.
2. For a recent review of alkene carbometallation (including carbolithiation) see P. Knochel, in Comprehensive Organic Synthesis, Pergamon, Oxford, 1991, vol. 4, ch. 4.4; see also B. J. Wakefield, The Chemistry of Organolithium Compounds, Pergamon, Oxford, 1974, section 7.1.
3. M. Merton, Anionic Polymerisation: Principles and Practice, Academic Press, New York, 1983; R. Waach and M. A. Doran, J. Org. Chem., 1967, 32, 3395 and references cited therein.
4. M. Merton, Anionic Polymerisation: Principles and Practice, Academic Press, New York, 1983; R. Waach and M. A. Doran, J. Org. Chem., 1967, 32, 3395 and references cited therein.
5. T. Fujita, S. Watanabe, K. Suga and H. Nakayama, Synthesis, 1979, 310; H. Pines and N. E. Sartoris, J. Org. Chem., 1969, 34, 2113 and references cited therein.
6. T. Fujita, S. Watanabe, K. Suga and H. Nakayama, Synthesis, 1979, 310; H. Pines and N. E. Sartoris, J. Org. Chem., 1969, 34, 2113 and references cited therein.
7. The process can be facilitated by transmetallation using transition metal salts or complexes: see ref. 1 and L. S. Hegedus, in Comprehensive Organic Synthesis, Pergamon, Oxford, 1991, vol. 4, ch. 3.2.
8. K. Ziegler, F. Crössman, H. Kleiner and O. Schäfer, Liebigs Ann. Chem., 1929, 473, 1; Y. Okamoto, M. Kato and H. Yuki, Bull. Chem. Soc. Jpn., 1969, 42, 760; G. Fraenkel, D. Estes and M. J. Geckle, J. Organomet. Chem., 1980, 185, 147; S. Klein, I. Marek, J.-F. Poisson and J.-F. Normant, J. Am. Chem. Soc., 1995, 117, 8853 and references cited therein.
9. K. Ziegler, F. Crössman, H. Kleiner and O. Schäfer, Liebigs Ann. Chem., 1929, 473, 1; Y. Okamoto, M. Kato and H. Yuki, Bull. Chem. Soc. Jpn., 1969, 42, 760; G. Fraenkel, D. Estes and M. J. Geckle, J. Organomet. Chem., 1980, 185, 147; S. Klein, I. Marek, J.-F. Poisson and J.-F. Normant, J. Am. Chem. Soc., 1995, 117, 8853 and references cited therein.
10. K. Ziegler, F. Crössman, H. Kleiner and O. Schäfer, Liebigs Ann. Chem., 1929, 473, 1; Y. Okamoto, M. Kato and H. Yuki, Bull. Chem. Soc. Jpn., 1969, 42, 760; G. Fraenkel, D. Estes and M. J. Geckle, J. Organomet. Chem., 1980, 185, 147; S. Klein, I. Marek, J.-F. Poisson and J.-F. Normant, J. Am. Chem. Soc., 1995, 117, 8853 and references cited therein.
11. K. Ziegler, F. Crössman, H. Kleiner and O. Schäfer, Liebigs Ann. Chem., 1929, 473, 1; Y. Okamoto, M. Kato and H. Yuki, Bull. Chem. Soc. Jpn., 1969, 42, 760; G. Fraenkel, D. Estes and M. J. Geckle, J. Organomet. Chem., 1980, 185, 147; S. Klein, I. Marek, J.-F. Poisson and J.-F. Normant, J. Am. Chem. Soc., 1995, 117, 8853 and references cited therein.
12. J. A. Landgrebe and J. D. Shoemaker, J. Am. Chem. Soc., 1967, 89, 4465.
13. R. Waack and M. A. Doran, J. Organomet. Chem., 1971, 29, 329; see also G. Fraenkel, M. J. Geckle, A. Kaylo and D. W. Estes, J. Organomet. Chem., 1980, 197, 249 and references cited therein.
14. R. Waack and M. A. Doran, J. Organomet. Chem., 1971, 29, 329; see also G. Fraenkel, M. J. Geckle, A. Kaylo and D. W. Estes, J. Organomet. Chem., 1980, 197, 249 and references cited therein.
15. W. F. Bailey and E. R. Punzalan, J. Org. Chem., 1990, 55, 5404; E. Negishi, D. R. Swanson and C. J. Rousset, J. Org. Chem., 1990, 55, 5406.
16. W. F. Bailey and E. R. Punzalan, J. Org. Chem., 1990, 55, 5404; E. Negishi, D. R. Swanson and C. J. Rousset, J. Org. Chem., 1990, 55, 5406.
17. See J. A. Seijas, M. P. Vázquez-Tato, L. Castedo, R. J. Estévez and M. Ruíz, J. Org. Chem., 1992, 57, 5283.