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Paper | Regular issue | Vol 43, No. 9, 1996, pp.1937-1942
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7518
Substituent Effect of the Fluorine Atom on Electrophilic Deuteration of Benzo[h]quinoline

Wei Wu, Ken-ichi Saeki,* and Yutaka Kawazoe

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan


Substituent effect of the fluorine atom on electrophillic substitution using the deuterium cation was examines by treating monofluorinated derivatives of benzo[h]quinoline with 96% D2SO4 at 80°C. The effect of the fluorine atom could not simply be explained by potent electron-withdrawing I-effect and electron-donating R-effect. The observed reaction rates were not simply correlated either with the stability of the σ-complexes estimated by a semiempirical molecular orbital MOPAC PM3 method. A fair correlation was found but not sufficiently for quantitative prediction of the rate.