NUCLEAR MAGNETIC RESONANCE STUDIES OF ENOL-ENOL AND KETO-ENOL EQUILIBRIA IN SUBSTITUTED BENZOYLACETONES

被引：84
作者：
SARDELLA, DJ
HEINERT, DH
SHAPIRO, BL
机构：
[1] Department of Chemistry, Illinois Institute of Technology, Chicago
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1969年 / 34卷 / 10期
关键词：
D O I：
10.1021/jo01262a004
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Nmr investigation of a series of para-substituted benzoylacetones has established that they exist largely (75-98%) as chelated cis-enols. Long-range coupling constants suggest that the benzoyl carbonyl group enolizes, forming the cinnamoyl chromophore, and that little benzoylethylene enol is present. Substituent effects on the keto-enol equilibrium are discussed. It has been found that the rule that electron-releasing groups stabilize adjacent carbonyl groups is valid in these systems. © 1969, American Chemical Society. All rights reserved.
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页码：2817 / &
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