Polarographic Reduction of 1,2,4-Benzothiadiazine-1,1-Dioxides and Related Compounds.

Cohen, Allen I.; Keeler, Barbara T.; Coy, N. H.; Yale, Harry L.

doi:10.1021/ac60182a018

Cited by 36 publications

(9 citation statements)

References 15 publications

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“…In aqueous solution, it has been reported that the successive reductive removal of the three fluorine atoms of trifluoromethyl compounds can be carried out at a single potential (-1.7 V in the case of TFMA) (8,9,13). For such a cleavage the presence of an activating group in the molecule is clearly necessary as demonstrated by the fact that trifluoromethylbenzene itself is non-reducible even at more cathodic potentials than -2.0 V vs. SCE (13), while for aromatic compounds bearing a sulfamyl function, a trifluoromethyl substituent is reduced to the methyl group at -1.76 V in aqueous solution (8).…”

Section: C-ohmentioning

confidence: 99%

“…However, in aqueous solutions, numerous carbonyl compounds are known to be subject to complex equilibria involving hydration-dehydration of the carbonyl group and keto-enol and acid-base equilibria; these result in the formation of both geminal-diols and enols or carbanion enolates according to the pH (5-7). Moreover, the reduction of trifluoromethyl compounds in aqueous and nonaqueous solutions may also involve C-F bond fission (8)(9)(10)(11)(12)(13). In this work, both the electrochemical and spectroscopic behavior of TFMA have been investigated in various protic solvents such as aqueous, micellar, and ethanolic solutions.…”

mentioning

confidence: 99%

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Electrochemical and spectroscopic behavior of trifluoromethylacetophenone in aqueous and micellar medium

Liotier¹,

Mousset²,

Mousty³

1995

Can. J. Chem.

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The electrochemical behavior of 4-trifluoromethylacetophenone (TFMA) has been studied in aqueous (2 ≤ pH ≤ 10), micellar, and ethanolic solutions using polarographic techniques. A slow hydration process of the carbonyl group has been observed by means of polarography and UV–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 4-methylacetophenone, which is reduced at this potential with formation of the carbinol and of symmetrical and dissymmetrical pinacols. 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. Keywords: 4-trifluoromethylacetophenone, 4-methylacetophenone, electroreduction, micellar medium, chiral surfactants, hydration, C—F bond fission.

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Section: C-ohmentioning

confidence: 99%

mentioning

confidence: 99%

Electrochemical and spectroscopic behavior of trifluoromethylacetophenone in aqueous and micellar medium

Liotier¹,

Mousset²,

Mousty³

1995

Can. J. Chem.

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show abstract

“…The equipment and procedure have been discussed (2). The steroids investigated have been prepared and characterized by various members of this laboratory.…”

Section: Methodsmentioning

confidence: 99%

“…The capillary characteristics of the dropping mercury electrode were determined at various voltages and the appropriate value was used in the calculation of the diffusion current constant, Id (2). The temperature of the solution was 25°± 0.5°C.…”

Section: Methodsmentioning

confidence: 99%