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

Aleksandra A. Zagulyaeva; Mekhman S. Yusubov; Viktor Zhdankin

doi:10.1021/jo902733f

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

Aleksandra A. Zagulyaeva
, Mekhman S. Yusubov
, Viktor Zhdankin

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

72 Scopus citations

Abstract

"Chemical Equation Presented" [Bis(trifiuoroacetoxy)iodo] perfiuoroalkanes C_nF_2n+1I(OC-OCF₃)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_nF_2n+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.

Original language	English (US)
Pages (from-to)	2119-2122
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	75
Issue number	6
DOIs	https://doi.org/10.1021/jo902733f
State	Published - Mar 19 2010

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10.1021/jo902733f

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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. / Zagulyaeva, Aleksandra A.; Yusubov, Mekhman S.; Zhdankin, Viktor.
In: Journal of Organic Chemistry, Vol. 75, No. 6, 19.03.2010, p. 2119-2122.

Research output: Contribution to journal › Article › peer-review

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title = "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",

abstract = "{"}Chemical Equation Presented{"} [Bis(trifiuoroacetoxy)iodo] perfiuoroalkanes CnF2n+1I(OC-OCF3)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, CnF2n+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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AU - Zagulyaeva, Aleksandra A.

AU - Yusubov, Mekhman S.

AU - Zhdankin, Viktor

PY - 2010/3/19

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N2 - "Chemical Equation Presented" [Bis(trifiuoroacetoxy)iodo] perfiuoroalkanes CnF2n+1I(OC-OCF3)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, CnF2n+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.

AB - "Chemical Equation Presented" [Bis(trifiuoroacetoxy)iodo] perfiuoroalkanes CnF2n+1I(OC-OCF3)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, CnF2n+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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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

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