A General and Convenient Preparation of [Bis(trifluoroacetoxy)iodo]perfluoroalkanes and [Bis(trifluoroacetoxy)iodo]arenes by Oxidation of Organic Iodides Using Oxone and Trifluoroacetic Acid

[Bis(trifluoroacetoxy)iodo]perfluoroalkanes C n F2n+1I(OCOCF3)2 (n = 4, 6, 8, 10, 12) can be conveniently prepared by the oxidation of the corresponding perfluoroalkyl iodides with Oxone in trifluoroacetic acid at room temperature and subsequently converted to the stable [hydroxy(tosyloxy)iodo]perfl...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 75; no. 6; pp. 2119 - 2122
Main Authors Zagulyaeva, Aleksandra A, Yusubov, Mekhman S, Zhdankin, Viktor V
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.03.2010
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
BIS(TRIFLUOROACETATE) ADDUCTS
CF3(CF2)(N-1)I(OCOCF3)
DIRECTIONS
FLUOROUS ALKYL IODIDES
HYPERVALENT IODINE REAGENTS
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Summary:[Bis(trifluoroacetoxy)iodo]perfluoroalkanes C n F2n+1I(OCOCF3)2 (n = 4, 6, 8, 10, 12) can be conveniently prepared by the oxidation of the corresponding perfluoroalkyl iodides with Oxone in trifluoroacetic acid at room temperature and subsequently converted to the stable [hydroxy(tosyloxy)iodo]perfluoroalkanes, C n F2n+1I(OH)OTs, by treatment with p-toluenesulfonic acid. This general and convenient procedure has been further extended to the synthesis of various [bis(trifluoroacetoxy)iodo]arenes, ArI(OCOCF3)2.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo902733f