ELECTROCHEMICAL AND SPECTROSCOPIC BEHAVIOR OF TRIFLUOROMETHYLACETOPHENONE IN AQUEOUS AND MICELLAR MEDIUM

被引：8

作者：

LIOTIER, E ^{[1
]}

MOUSSET, G ^{[1
]}

MOUSTY, C ^{[1
]}

机构：

[1] UNIV CLERMONT FERRAND,ELECTROCHIM ORGAN THERMODYNAM & ELECTROCHIM SOLUT,CNRS,URA 434,F-63177 CLERMONT FERRAND,FRANCE

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1995年 / 73卷 / 09期

关键词：

4-TRIFLUOROMETHYLACETOPHENONE; 4-METHYLACETOPHENONE; ELECTROREDUCTION; MICELLAR MEDIUM; CHIRAL SURFACTANTS; HYDRATION; C-F BOND FISSION;

D O I：

10.1139/v95-184

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The electrochemical behavior of 4-trifluoromethylacetophensne (TFMA) has been studied in aqueous (2 less than or equal to pH less than or equal to 10), micellar, and ethanolic solutions using polarographic techniques. A slow hydration process of the carbonyl group has been observed by means of polarography and W-visible spectrophotometry. Besides the well-known pH dependence of the electroreduction of aromatic ketones, C-F bond cleavages concomitant to the ketone reduction occur under electrolysis conditions in alkaline medium (pH = 10) at a very negative potential (-1.7 V), leading to the formation of 3-methylacetophenone, which is reduced at this potential with formation of the carbinol and of symmetrical and dissymmetrical pinncols. Finally, the reduction of TFMA has been performed in the presence of chiral surfactants in order to test their ability to induce an asymmetric induction.

引用

页码：1488 / 1496

页数：9

共 27 条

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ANDRIEUX CP, 1973, B SOC CHIM FR II-CH, P2090

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