Radical Reduction of C-Cl Bonds in Chlorofluoro Ethers

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Title:Radical Reduction of C-Cl Bonds in Chlorofluoro Ethers
Creators:
Liška, František
Fikar, Jiří
Kuzmič, Petr
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 3, pp. 565-574

Abstract

Reduction of C-Cl bonds in 2,2-dichloro-1,1,2-trifluoroethyl trichloromethyl ether (<i>I</i>), 2-chloro-1,1,2-trifluoroethyl trichloromethyl ether (<i>II</i>), and 2,2-dichloro-1,1,2-trifluoroethyl dichloromethyl ether (<i>III</i>) with 2-propanol, 2-butanol, cyclohexanol, tetrahydrofurane, diethyl ether, and 1,3-dioxolane initiated photochemically and by radiation has been investigated. Beside the main reduction products - 2-chloro-1,1,2-difluoroethyl trichloromethyl ether (<i>IV</i>) and 2-chloro-1,1,2-difluoroethyl chloromethyl ether (<i>V</i>) - it was also possible to prove the formation of 1,2-dichloro-1,2-bis(2-chloro-1,1,2-trifluoroethoxy)ethane (<i>VI</i>), 1-chloro-1,2-bis(2-chloro-1,1,2-trifluoroethoxy)ethane (<i>VII</i>), and 1,2-dichloro-1,2-bis(2-chloro-1,1,2-trifluoroethoxy)ethene (<i>VIII</i>). The structure of products was confirmed by elemental analysis, MS, IR, <sup>1</sup>H NMR and <sup>19</sup>F NMR spectra and by GLC comparison of the elution times with those of standards. The relative reduction ability of the solvents used in the reduction rate order of C-Cl bonds in the compounds (CCl<sub>3</sub> &gt; CFCl<sub>2</sub> &gt; CHCl<sub>2</sub> and CFClH) are given.

Title:Radical Reduction of C-Cl Bonds in Chlorofluoro Ethers
Creators:
Liška, František
Fikar, Jiří
Kuzmič, Petr
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:58
Number:3
Page Range:pp. 565-574
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19930565UNSPECIFIED
ID Code:180
Item Type:Article
Deposited On:06 Feb 2009 16:58
Last Modified:06 Feb 2009 15:58

Citation

Liška, František; Fikar, Jiří; Kuzmič, Petr (1993) Radical Reduction of C-Cl Bonds in Chlorofluoro Ethers. Collection of Czechoslovak Chemical Communications, 58 (3). pp. 565-574. ISSN 0010-0765

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