On the dichotomy of the SN2/ET reaction pathways: An apparent SN2 reactivity in the reaction of naphthalene dianion with alkyl fluorides

Tetrahedron Letters

Volumn 44, Issue 6, 2003, Pages 1309-1312

  Herrera, Raquel P ^a   Guijarro, Albert ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ANION; FLUORIDE; HALIDE; HEPTANE; LITHIUM DERIVATIVE; NAPHTHALENE DERIVATIVE; OCTANE; RADICAL;

ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; ELECTRON TRANSPORT; GAS LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

EID: 0037415468     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02808-3     Document Type: Article

References (15)

1. Garst J.F. Acc. Chem. Res. 4:1971;400.
2. Garst J.F., Barton F.E. II. Tetrahedron Lett. 7:1969;587.
3. Garst J.F., Barton F.E. II. J. Am. Chem. Soc. 96:1974;523.
4. Yus M., Herrera R.P., Guijarro A. Chem. Eur. J. 8:2002;2574.
5. Yus M., Herrera R.P., Guijarro A. Tetrahedron Lett. 42:2001;3455.
6. Guijarro A., Rieke R.D. Angew. Chem., Int. Ed. 37:1998;1679.
7. 2-Fluorooctane was obtained by nucleophilic substitution on the 2-octyl tosylate using KF. See: Filipo, J. S., Jr.; Romano, L. J. J. Org. Chem. 1975, 40, 1514. 2-Fluoro-2-methylheptane was obtained by treatment of 2-methyl-2-octanol with HF-Py.
8. Guijarro A., Rosenberg D.M., Rieke R.D. J. Am. Chem. Soc. 121:1999;4155.
9. Marcus. Pure Appl. Chem. 69:1997;13.
10. N2, see: (a) Daasberg, K.; Christensen, T. B. Acta Chem. Scand. 1995, 49, 128; (b) Huang, Y.; Wayner, D. D. M. J. Am. Chem. Soc. 1994, 116, 2157; (c) Bilkis, I. I.; Selivanov, B. A.; Shteingarts, V. D. Res. Chem. Intermed. 1993, 19, 463.
11. For anionic cyclization rates of 5-hexenyllithium at 0°C, see: Bailey W.F., Patricia J.J., DelGobbo V.C., Jarret R.M., Okarma P.J. J. Org. Chem. 50:1985;2000.
12. Eberson L. Acta Chem. Scand. B. 36:1982;533.
13. Leroy J., Hebert E., Walkselman C. J. Org. Chem. 44:1979;3406.
14. Malissard M., Mazaleyrat J.-P., Welvart Z. J. Am. Chem. Soc. 99:1977;6933.
15. Hebert E., Mazaleyrat J.-P., Welvart Z., Nadjo L., Savéant J.-L. Nouv. J. Chim. 9:1985;75.