Synthesis of Trifluoromethylated Amines Using 1,1-Bis(dimethylamino)-2,2,2-trifluoroethane

Lewis acid-catalyzed deamination of aminal, 1,1-bis(dimethylamino)-2,2,2-trifluoroethane, using ZnI2 in ether, generates the 2,2,2-trifluoro-1,1-dimethylaminoethyl carbocation, which undergoes synthetically useful electrophilic reactions with alkynes, a variety of electron-rich alkenes, and TMS cyan...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 65; no. 7; pp. 2134 - 2137
Main Authors Xu, Yuelian, Dolbier, William R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.04.2000
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
ETHERS
FACILE SYNTHESIS
ELECTROLYTIC REACTIONS
ANODIC METHOXYLATION
MANNICH REACTIONS
BUILDING-BLOCKS
FLUOROORGANIC COMPOUNDS
DERIVATIVES
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Summary:Lewis acid-catalyzed deamination of aminal, 1,1-bis(dimethylamino)-2,2,2-trifluoroethane, using ZnI2 in ether, generates the 2,2,2-trifluoro-1,1-dimethylaminoethyl carbocation, which undergoes synthetically useful electrophilic reactions with alkynes, a variety of electron-rich alkenes, and TMS cyanide to form trifluoromethylated alkynylamines, homoallylic amines, α,β-unsaturated ketones, and cyanoamines in fair to good yields.
Bibliography:istex:B6B5DEE95BCCF257826C57CDB029A2636AE11DFE
ark:/67375/TPS-5QSJB49W-5
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo991750y