Electroreductive Additions of Aromatic Dichalcogenides to Fluorinated Ethenes

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Title:Electroreductive Additions of Aromatic Dichalcogenides to Fluorinated Ethenes
Creators:
Dvořák, David
Neugebauerová, Eva
Liška, František
Ludvík, Jiří
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 3, pp. 378-386
Uncontrolled Keywords:Diphenyl dichalcogenides, Electroreductive addition, Diphenyl diselenide, Chlorofluoroethenes, Electrochemistry, Diphenyl disulfide

Abstract

Intermediates and products formed during the electrochemical reduction of diphenyl disulfide (<strong>1</strong>) add to chlorotrifluoroethene (<strong>3</strong>) under the formation of 2-chloro-1,1,2-trifluoroethyl phenyl sulfide (<strong>5</strong>) and the <i>E/Z</i> isomers of 2-chloro-1,2-difluoroethenyl phenyl sulfide (<strong>6</strong>). The analogous reaction with 1,2-dichlorodifluoroethene (<strong>4</strong>) led to a mixture of <i>E/Z</i> isomers of <strong>6</strong>. Electrochemically reduced diphenyl diselenide (<strong>2</strong>) reacted with <strong>3</strong> giving rise to 2-chloro-1,1,2-trifluoroethyl phenyl selenide (<strong>7</strong>) whereas the reaction with <strong>4</strong> does not proceed. Addition of disulfide <strong>1</strong> to <strong>4</strong> gives evidence of the participation of the radical PhS<sup><strong>Ib></sup>. With diselenide <strong>2</strong>, an analogous radical addition reaction was not observed. This is consistent with other experiments suggesting different mechanisms of reductive cleavage of the S-S and Se-Se bonds and the absence of radicals PhSe<sup><strong>Ib></sup> in the latter.

Title:Electroreductive Additions of Aromatic Dichalcogenides to Fluorinated Ethenes
Creators:
Dvořák, David
Neugebauerová, Eva
Liška, František
Ludvík, Jiří
Uncontrolled Keywords:Diphenyl dichalcogenides, Electroreductive addition, Diphenyl diselenide, Chlorofluoroethenes, Electrochemistry, Diphenyl disulfide
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:3
Page Range:pp. 378-386
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980378UNSPECIFIED
ID Code:1305
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Dvořák, David; Neugebauerová, Eva; Liška, František; Ludvík, Jiří (1998) Electroreductive Additions of Aromatic Dichalcogenides to Fluorinated Ethenes. Collection of Czechoslovak Chemical Communications, 63 (3). pp. 378-386. ISSN 0010-0765

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