Radical Additions to Fluoroolefins: Experimental Evidence for a Free-Radical Chain Mechanism in the Photo-Initiated Addition of Alcohols to Fluoroolefins

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Title:Radical Additions to Fluoroolefins: Experimental Evidence for a Free-Radical Chain Mechanism in the Photo-Initiated Addition of Alcohols to Fluoroolefins
Creators:
Paleta, Oldřich
Kvíčala, Jaroslav
Budková, Zuzana
Timpe, Hans-Joachim
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 60, 4, pp. 636-644

Abstract

<p>Photo-initiated addition of 2-propanol to two fluoroolefinic compounds, i.e. methyl 2,4,4,5,6,6-hexafluoro-3-oxa-2-(trifluoromethyl)hex-5-enoate (<i>IV</i>) containing perfluoroallyloxy group and 8,9-dichloro-1,1,2,4,4,5,7,7,8,9,9-undecafluoro-3,6-dioxa-5-(t rifluoromethyl)dodec-1-ene (<i>V</i>) containing trifluorovinyloxy group were used to verify a free-radical chain mechanism by means of quantum yield measurements based on substrate-decay kinetic. UV-Light energy (254 nm) was transferred to the reaction system via triplet-excited acetone. Quantum yields Fi of the addition products (<i>X</i>, <i>XI</i>) reached values 68 and 42, respectively, and thus confirmed the chain mechanism. The olefinic compounds IV and V were synthesized on the basis of the reaction of 2,3-dichloro-2,3,3-trifluoropropanoyl fluoride (<i>I</i>) with hexafluoropropene-1,2-oxide. The photoaddition of 2-propanol to both olefins took place with complete regioselectivity.

Title:Radical Additions to Fluoroolefins: Experimental Evidence for a Free-Radical Chain Mechanism in the Photo-Initiated Addition of Alcohols to Fluoroolefins
Creators:
Paleta, Oldřich
Kvíčala, Jaroslav
Budková, Zuzana
Timpe, Hans-Joachim
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:60
Number:4
Page Range:pp. 636-644
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19950636UNSPECIFIED
ID Code:752
Item Type:Article
Deposited On:06 Feb 2009 17:03
Last Modified:06 Feb 2009 16:03

Citation

Paleta, Oldřich; Kvíčala, Jaroslav; Budková, Zuzana; Timpe, Hans-Joachim (1995) Radical Additions to Fluoroolefins: Experimental Evidence for a Free-Radical Chain Mechanism in the Photo-Initiated Addition of Alcohols to Fluoroolefins. Collection of Czechoslovak Chemical Communications, 60 (4). pp. 636-644. ISSN 0010-0765

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