Synthesis of and Analysis of Thiol Additions to .beta.-Alkyl-.alpha.,.beta.-unsaturated Trifluoromethyl Ketones

A series of beta-alkyl-alpha,beta-unsaturated trifluoromethyl ketones have been prepared from the corresponding alpha-acetylenic trifluoromethyl ketones. The addition of sulfur nucleophiles was shown by chemical and F-19 NMR studies to proceed exclusively by 1,4-addition with no indication of any 1,...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 59; no. 5; pp. 957 - 962
Main Authors Linderman, Russell J, Jamois, Eric A, Tennyson, Scott D
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.03.1994
Amer Chemical Soc
Subjects
Aliphatic compounds
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ALCOHOLS
HALIDES
GLUTATHIONE TRANSFERASES
ACID
GEOMETRIC ISOMERS
ALDEHYDES
INHIBITORS
FACILE
PERFLUOROALKYLATION
VITAMIN-A
Thiol
Acetylenic compound
Hydrocarbon
Lithium Tetrahydroaluminates
Regioselectivity
Haloketone
Ketosulfide
Saturated aliphatic compound
Addition reaction
Oxidation
Fluorine Organic compounds
Enone
Nucleophilic addition
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Summary:A series of beta-alkyl-alpha,beta-unsaturated trifluoromethyl ketones have been prepared from the corresponding alpha-acetylenic trifluoromethyl ketones. The addition of sulfur nucleophiles was shown by chemical and F-19 NMR studies to proceed exclusively by 1,4-addition with no indication of any 1,2-addition products. The unsaturated trifluoromethyl ketones have been shown to be effective inhibitors of rat cytosolic glutathione-S-transferase.
Bibliography:ark:/67375/TPS-0FWX2VS7-6
istex:07451EB86AAA474866C393E47793C8684488C783
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00084a009