Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.