Synthesis and experimental study of through-space hydrogen-fluorine and carbon-fluorine spin-spin coupling in 4,5-substituted 1-acetyl-8-fluoronaphthalenes.
The synthesis and NMR study (1H, 13C, and 19F) of a complete series of 4,5-substituted 1-acetyl-8-fluoronaphthalenes are reported. This data revealed a 6J(H,F) and a 5J(C,F) through space coupling between the fluorine and the methyl on the acetyl group (1H and 13C). The magnitude of this coupling constant changes depending on the nature of the substituent at C-4, the internuclear distance, and the solvent.
Jaime-Figueroa
S
S
Medicinal Chemistry Department, Roche Bioscience, Palo Alto, CA 94303, USA. saul.jaime@roche.com
Kurz
L J
LJ
Liu
Y
Y
Cruz
R
R
D002244:Carbon / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009281:Naphthalenes / Q000737:chemistry*
D009281:Naphthalenes; D005461:Fluorine; D002244:Carbon; D006859:Hydrogen