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Electrochemical reduction of 1,1-diaryl-substituted ethenes in dimethylformamide

Fruianu, Michelina and Marchetti, Mauro and Melloni, Giovanni and Sanna, Gavino and Seeber, Renato (1994) Electrochemical reduction of 1,1-diaryl-substituted ethenes in dimethylformamide. Journal of the Chemical Society. Perkin Transactions 2, Vol. 1994 (9), p. 2039-2044. ISSN 0300-9580. Article.

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DOI: 10.1039/P29940002039

Abstract

The cathodic behaviour of 1,1-diaryl-substituted ethenes (Ar)PhC CH2(where Ar = phenyl-, 2-naphthyl-, 2-pyridyl-, 2-thienyl-, 2-furyl-) at a Hg cathode in N,N-dimethylformamide (DMF) and 0.1 mol dm–3 tetraethylammonium tetrafluoroborate (TEAF), was investigated by cyclic voltammetry and controlled potential electrolysis experiments. In cyclic voltammetry, at a potential scan rate of 0.2 V s –1, all substrates showed an irreversible reduction peak [(Ep,c) between –2.27 and –2.54 V vs. saturated calomel electrode (SCE)]. Controlled potential coulometries indicated that the apparent charge number of the process involved ranges from 1 to 2. The reduction products were characterised as (Ar)PhCH–Me (1-aryl-1-phenylethanes) and (Ar)PhCH–[CH2]2–CHPh(Ar)(1,4-diaryl-1,4-diphenylbutanes). The charge number of the process and the ratio between the two different reduction products depended strongly on the structure and concentration of the substrate. Exhaustive electrolyses performed in the presence of variable amounts of D2O or in [2H7]DMF allowed us to suggest that two distinct pathways are involved in the reduction process, leading to the monomeric and dimeric product, respectively. Hypotheses on the nature of the two reduction mechanisms are discussed.

Item Type:Article
ID Code:3692
Status:Published
Refereed:Yes
Uncontrolled Keywords:1,1-diaryl-substituted ethenes, dimethylformamide, electrochemical reduction
Subjects:Area 03 - Scienze chimiche > CHIM/01 Chimica analitica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:Royal Society of Chemistry
ISSN:0300-9580
Deposited On:07 Apr 2010 12:00

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