Radical reaction using an organocopper reagent derived from ethyl bromodifluoroacetate

In our previous work, reaction of ethyl bromodifluoroacetate (1) in the presence of Cu powder with olefins activated by an electron-withdrawing group gave the Michael-type adducts through an anionic intermediate. The same reaction with non-activated olefins was found to give addition products by a r...

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Published inCollection of Czechoslovak chemical communications Vol. 67; no. 9; pp. 1285 - 1295
Main Authors Sato, K, Ogawa, Y, Tamura, M, Harada, M, Ohara, T, Omote, M, Ando, A, Kumadaki
Format Journal Article
LanguageEnglish
Published PRAGUE 6 Inst Organic Chem And Biochem 01.01.2002
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ethyl bromodifluoroacetate
copper powder
ACID
radicals
alkenes
fluorinated compounds
radical additions
fluorine
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Abstract In our previous work, reaction of ethyl bromodifluoroacetate (1) in the presence of Cu powder with olefins activated by an electron-withdrawing group gave the Michael-type adducts through an anionic intermediate. The same reaction with non-activated olefins was found to give addition products by a radical mechanism. The radical intermediate from alpha-methyl-styrene was stabilized by a benzene ring and gave novel dimerization products. This reaction with 1-decene provided a convenient route to 2,2-difluorododecanoic acid.
AbstractList In our previous work, reaction of ethyl bromodifluoroacetate (1) in the presence of Cu powder with olefins activated by an electron-withdrawing group gave the Michael-type adducts through an anionic intermediate. The same reaction with non-activated olefins was found to give addition products by a radical mechanism. The radical intermediate from alpha-methyl-styrene was stabilized by a benzene ring and gave novel dimerization products. This reaction with 1-decene provided a convenient route to 2,2-difluorododecanoic acid.
Author Tamura, M
Ohara, T
Omote, M
Ando, A
Ogawa, Y
Kumadaki
Sato, K
Harada, M
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Keywords ethyl bromodifluoroacetate
copper powder
ACID
radicals
alkenes
fluorinated compounds
radical additions
fluorine
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Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Title Radical reaction using an organocopper reagent derived from ethyl bromodifluoroacetate
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