ELECTRONIC PROPERTIES OF 3-MEMBERED RINGS .2. TRANSMISSION OF CONJUGATION BY CYCLOPROPANE RING

被引:55
作者
PEWS, RG
OJHA, ND
机构
[1] Hydrocarbons and Monomers Research Laboratory, Dow Chemical Company, Midland
关键词
D O I
10.1021/ja01049a012
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of p-fluoro-m′- and -p′-substituted 1,2-diphenylethanes (bibenzyls), 1,2-diphenylethylenes (stilbenes), and 1,2-diphenylcyclopropanes have been synthesized and their 19F nmr spectra determined in dilute benzene solution. A quantitative measure of the ability of the cyclopropyl ring to transmit conjugation in the ground electronic state has been made from a plot of the19F nmr shielding parameters vs. Taft´s σ˚ constant. The results of the present study show that the cyclopropyl ring is ~27% as effective as the vinyl moiety (relative to dimethylene) in its ability to transmit conjugation. © 1969, American Chemical Society. All rights reserved.
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页码:5769 / &
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