Reactivity in the upper limits of the reduction potential in solution: arene dianion intermolecular carbolithiation of alkenes

Tetrahedron Letters

Volumn 47, Issue 35, 2006, Pages 6267-6271

  Melero, Cristóbal ^a   Guijarro, Albert ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Alkenes; Arene dianion; Dearomatization; Intermolecular carbolithiation; Lithium

Indexed keywords

ALKENE DERIVATIVE; ANION; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CALCULATION; CHEMICAL REACTION; LITHIATION; PREDICTION;

EID: 33746272630     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.120     Document Type: Article

References (19)

1. Yus M. In: Rappoport Z., and Marek I. (Eds). The Chemistry of Organolithium Compounds Vol. 1 (2004), Wiley & Sons, Chichester 657-747 Part 1
2. Yus M., Herrera R.P., and Guijarro A. Chem. Eur. J. 8 (2002) 2574-2584
3. Yus M., Herrera R.P., and Guijarro A. Tetrahedron Lett. 42 (2001) 3455-3458
4. Herrera R.P., Guijarro A., and Yus M. Tetrahedron Lett. 44 (2003) 1313-1316
5. Meerholz K., and Heinze J. J. Am. Chem. Soc. 111 (1989) 2325-2326
6. Rabinovitz M. Top. Curr. Chem. 146 (1988) 99-169
7. Minsky A., Meyer A.Y., and Rabinovitz M. Tetrahedron Lett. 23 (1982) 5351-5354
8. Minsky A., Meyer A.Y., and Rabinovitz M. Tetrahedron 41 (1985) 785-791
9. Guerra M. Chem. Phys. Lett. 197 (1992) 205-212
10. Sommerfeld T. J. Am. Chem. Soc. 124 (2002) 1119-1124
11. Boldyrev A.I., Gutowski M., and Simons J. Acc. Chem. Res. 29 (1996) 497-502
12. Brooks J.J., Rhine W., and Stucky G.D. J. Am. Chem. Soc. 94 (1972) 7346-7351
13. Muellen K. Helv. Chim. Acta 61 (1978) 1296-1304
14. Sidorov A.N. Opt. Spektrosk. 47 (1979) 678-683
15. Chem. Abstr. 92 (1980) 110107
16. Devlin J.P., McKennis J.S., Thornton C., and Moore J.C. J. Phys. Chem. 86 (1982) 2613-2616
17. Eisch J.J. J. Org. Chem. 28 (1963) 707-710
18. Barlett P.D., Tauber S.J., and Weber W.P. J. Am. Chem. Soc. 91 (1969) 6362-6366
19. 28O: 284.2140; found 284.2092.