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 Vladimirovich Zhdankin

Research School of Chemistry & Applied Biomedical Sciences

Research output: Contribution to journal › Article

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
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
Publication status	Published - 19 Mar 2010

Fingerprint

ASJC Scopus subject areas

Organic Chemistry

Cite this

Zagulyaeva, A. A., Yusubov, M. S., & Zhdankin, V. V. (2010). 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. Journal of Organic Chemistry, 75(6), 2119-2122. https://doi.org/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. / Zagulyaeva, Aleksandra A.; Yusubov, Mekhman S.; Zhdankin, Viktor Vladimirovich.

In: Journal of Organic Chemistry, Vol. 75, No. 6, 19.03.2010, p. 2119-2122.

Research output: Contribution to journal › Article

@article{d111ebf9c660439584c045b7b572ed3f,

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.",

author = "Zagulyaeva, {Aleksandra A.} and Yusubov, {Mekhman S.} and Zhdankin, {Viktor Vladimirovich}",

year = "2010",

month = mar

day = "19",

doi = "10.1021/jo902733f",

language = "English",

volume = "75",

pages = "2119--2122",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - 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

AU - Zagulyaeva, Aleksandra A.

AU - Yusubov, Mekhman S.

AU - Zhdankin, Viktor Vladimirovich

PY - 2010/3/19

Y1 - 2010/3/19

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.

UR - http://www.scopus.com/inward/record.url?scp=77949812753&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77949812753&partnerID=8YFLogxK

U2 - 10.1021/jo902733f

DO - 10.1021/jo902733f

M3 - Article

C2 - 20163086

AN - SCOPUS:77949812753

VL - 75

SP - 2119

EP - 2122

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 6

ER -

Access to Document

10.1021/jo902733f