N-Perfluoroalkylsulfonylimido derivatives of arenecarboxylic acid amides and their oxidative aza Hofmann rearrangement

Lev M. Yagupolskii; Irina I. Maletina; Liubov V. Sokolenko; Yurii G. Vlasenko; Sergey A. Buth

doi:10.1016/j.jfluchem.2008.03.001

N-Perfluoroalkylsulfonylimido derivatives of arenecarboxylic acid amides and their oxidative aza Hofmann rearrangement

Lev M. Yagupolskii, Irina I. Maletina, Liubov V. Sokolenko, Yurii G. Vlasenko, Sergey A. Buth

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

9 Scopus citations

Abstract

The analogues of carboxamides in which the sp²-hybridized oxygen atom is replaced by more electron-withdrawing groups, {double bond, long}NSO₂CF₃ and {double bond, long}NSO₂C₄F₉, have been synthesized. The resulting N-perfluoroalkylsulfonyl arenecarboxamidines ArC({double bond, long}NSO₂R_f)NH₂ (R_f = CF₃, C₄F₉) undergo an oxidative Hofmann-type rearrangement to the corresponding carbodiimides ArN{double bond, long}C{double bond, long}NSO₂R_f under the action of (diacyloxyiodo)arenes. Rearrangement of related compounds ArC({double bond, long}NSO₂R)NH₂ (R = CH₃, Ph) containing fluorine-free substituents at the sulfonyl group also occurs in similar conditions. It was found that the reactivity of amidines rises with the increasing electron-withdrawing ability of the substituent R.

Original language	English (US)
Pages (from-to)	486-492
Number of pages	7
Journal	Journal of Fluorine Chemistry
Volume	129
Issue number	6
DOIs	https://doi.org/10.1016/j.jfluchem.2008.03.001
State	Published - Jun 2008
Externally published	Yes

Keywords

Amidines
Carbodiimides
Rearrangements
X-ray structure

ASJC Scopus subject areas

Biochemistry
Environmental Chemistry
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.jfluchem.2008.03.001

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@article{ada96c0fe4a54059b73706d0fbb5022a,

title = "N-Perfluoroalkylsulfonylimido derivatives of arenecarboxylic acid amides and their oxidative aza Hofmann rearrangement",

abstract = "The analogues of carboxamides in which the sp2-hybridized oxygen atom is replaced by more electron-withdrawing groups, {double bond, long}NSO2CF3 and {double bond, long}NSO2C4F9, have been synthesized. The resulting N-perfluoroalkylsulfonyl arenecarboxamidines ArC({double bond, long}NSO2Rf)NH2 (Rf = CF3, C4F9) undergo an oxidative Hofmann-type rearrangement to the corresponding carbodiimides ArN{double bond, long}C{double bond, long}NSO2Rf under the action of (diacyloxyiodo)arenes. Rearrangement of related compounds ArC({double bond, long}NSO2R)NH2 (R = CH3, Ph) containing fluorine-free substituents at the sulfonyl group also occurs in similar conditions. It was found that the reactivity of amidines rises with the increasing electron-withdrawing ability of the substituent R.",

keywords = "Amidines, Carbodiimides, Rearrangements, X-ray structure",

author = "Yagupolskii, {Lev M.} and Maletina, {Irina I.} and Sokolenko, {Liubov V.} and Vlasenko, {Yurii G.} and Buth, {Sergey A.}",

year = "2008",

month = jun,

doi = "10.1016/j.jfluchem.2008.03.001",

language = "English (US)",

volume = "129",

pages = "486--492",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier BV",

number = "6",

}

TY - JOUR

T1 - N-Perfluoroalkylsulfonylimido derivatives of arenecarboxylic acid amides and their oxidative aza Hofmann rearrangement

AU - Yagupolskii, Lev M.

AU - Maletina, Irina I.

AU - Sokolenko, Liubov V.

AU - Vlasenko, Yurii G.

AU - Buth, Sergey A.

PY - 2008/6

Y1 - 2008/6

N2 - The analogues of carboxamides in which the sp2-hybridized oxygen atom is replaced by more electron-withdrawing groups, {double bond, long}NSO2CF3 and {double bond, long}NSO2C4F9, have been synthesized. The resulting N-perfluoroalkylsulfonyl arenecarboxamidines ArC({double bond, long}NSO2Rf)NH2 (Rf = CF3, C4F9) undergo an oxidative Hofmann-type rearrangement to the corresponding carbodiimides ArN{double bond, long}C{double bond, long}NSO2Rf under the action of (diacyloxyiodo)arenes. Rearrangement of related compounds ArC({double bond, long}NSO2R)NH2 (R = CH3, Ph) containing fluorine-free substituents at the sulfonyl group also occurs in similar conditions. It was found that the reactivity of amidines rises with the increasing electron-withdrawing ability of the substituent R.

AB - The analogues of carboxamides in which the sp2-hybridized oxygen atom is replaced by more electron-withdrawing groups, {double bond, long}NSO2CF3 and {double bond, long}NSO2C4F9, have been synthesized. The resulting N-perfluoroalkylsulfonyl arenecarboxamidines ArC({double bond, long}NSO2Rf)NH2 (Rf = CF3, C4F9) undergo an oxidative Hofmann-type rearrangement to the corresponding carbodiimides ArN{double bond, long}C{double bond, long}NSO2Rf under the action of (diacyloxyiodo)arenes. Rearrangement of related compounds ArC({double bond, long}NSO2R)NH2 (R = CH3, Ph) containing fluorine-free substituents at the sulfonyl group also occurs in similar conditions. It was found that the reactivity of amidines rises with the increasing electron-withdrawing ability of the substituent R.

KW - Amidines

KW - Carbodiimides

KW - Rearrangements

KW - X-ray structure

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U2 - 10.1016/j.jfluchem.2008.03.001

DO - 10.1016/j.jfluchem.2008.03.001

M3 - Article

AN - SCOPUS:44649111829

SN - 0022-1139

VL - 129

SP - 486

EP - 492

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

IS - 6

ER -

N-Perfluoroalkylsulfonylimido derivatives of arenecarboxylic acid amides and their oxidative aza Hofmann rearrangement

Abstract

Keywords

ASJC Scopus subject areas

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