Dianions of 4-phenylbut-1-ene. Evidence for complex-induced proximity effects in the double metallation of hydrocarbons

Journal of the Chemical Society. Perkin Transactions 2

Volumn 9, Issue , 1996, Pages 2035-2039

  Mills, Nancy S ^a   Ruud, C Channing ^a  

^a TRINITY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842397033     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/p29960002035     Document Type: Article

References (21)

1. (a) N. S. Mills, J. Shapiro and M. Hollingsworth, J. Am. Chem. Soc., 1981, 103, 1263;
2. (b) A. I. Rusinko and N. S. Mills, J. Org. Chem., 1982, 47, 5198;
3. (c) N. S. Mills, J. Am. Chem. Soc., 1982, 104, 5689;
4. (d) N. S. Mills and A. I. Rusinko, J. Org. Chem., 1986, 51, 2567;
5. (e) S. D. Meyer, N. S. Mills, J. B. Runnels, B. de la Torre, C. C. Ruud and D. K. Johnson, J. Org. Chem., 1991, 56, 947.
6. J. Klein, A. Medlik-Balan, A. Y. Meyer and M. Chorev, Tetrahedron, 1976, 32, 1839.
7. Although these species are referred to as dianions, the carbon-lithium bonds possess appreciable covalent character.
8. J. Klein and A. Medlik, J. Chem. Soc., Chem. Commun., 1973, 275.
9. (a) P. Gund, J. Chem. Educ., 1972, 49, 100;
10. (b) R. A. Finnegan, Ann. N. Y. Acad. Sci., 1969, 152, 242;
11. (c) I. Agranat and A. Skancke, J. Am. Chem. Soc., 1985, 107, 867.
12. S. K. Arora, R. B. Bates, W. A. Beavers and R. S. Cutler, J. Am. Chem. Soc., 1975, 97, 6271.
13. 1a
14. D. Boerth and A. J. Streitwieser, J. Am. Chem. Soc., 1981, 103, 6443.
15. C. D. Broadus, J. Org. Chem., 1970, 35, 10.
16. F. Houle and W. Hinsberg, Surf. Science, 1995, 338, 329.
17. P. Beak and A. I. Meyers, Acc. Chem. Res., 1986, 19, 356.
18. I. Fleming and A. Pearce, J. Chem. Soc., Perkin Trans. 1, 1981, 251.
19. H. Nishiyama, K. Itagaki, K. Takahashi and K. Itoh, Tetrahedron Lett., 1981, 22, 1691.
20. 1H NMR spectra were deduced from isolated fractions of varying composition. The MS data are for the mixture.
21. R. B. Bates, J. B. A. Hess, C. A. Ogle and L. J. Schaad, J. Am. Chem. Soc., 1981, 103, 5052.