1,3-Dipolar cycloadditions of fluorinated nitrones with thioketones

Grzegorz Mlostoń; Emilia Obijalska; Małgorzata Celeda; Verena Mittermeier; Anthony Linden; Heinz Heimgartner

doi:10.1016/j.jfluchem.2014.05.015

1,3-Dipolar cycloadditions of fluorinated nitrones with thioketones

Grzegorz Mlostoń
, Emilia Obijalska
, Małgorzata Celeda
, Verena Mittermeier
, Anthony Linden
, Heinz Heimgartner

University of Lodz
University of Zurich

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

16 Scopus citations

Abstract

Fluorinated nitrones derived from fluoral and difluoroacetaldehyde react with thioketones via [3 + 2] cycloaddition yielding 1,4,2-oxathiazolidines in a regioselective manner. Unexpectedly, cycloaliphatic thioketones react faster than aromatic thioketones. Due to the presence of a fluorinated alkyl group, the cycloadducts display a remarkable stability and do not decompose at room temperature in the crystalline form nor in solution.

Original language	English
Pages (from-to)	27-32
Number of pages	6
Journal	Journal of Fluorine Chemistry
Volume	165
DOIs	https://doi.org/10.1016/j.jfluchem.2014.05.015
State	Published - Sep 2014
Externally published	Yes

Keywords

1;3-Dipolar cycloadditions
5-Membered heterocycles
Fluorinated heterocycles
Nitrones
Thioketones

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10.1016/j.jfluchem.2014.05.015

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title = "1,3-Dipolar cycloadditions of fluorinated nitrones with thioketones",

abstract = "Fluorinated nitrones derived from fluoral and difluoroacetaldehyde react with thioketones via [3 + 2] cycloaddition yielding 1,4,2-oxathiazolidines in a regioselective manner. Unexpectedly, cycloaliphatic thioketones react faster than aromatic thioketones. Due to the presence of a fluorinated alkyl group, the cycloadducts display a remarkable stability and do not decompose at room temperature in the crystalline form nor in solution.",

keywords = "1;3-Dipolar cycloadditions, 5-Membered heterocycles, Fluorinated heterocycles, Nitrones, Thioketones",

author = "Grzegorz Mlosto{\'n} and Emilia Obijalska and Ma{\l}gorzata Celeda and Verena Mittermeier and Anthony Linden and Heinz Heimgartner",

year = "2014",

month = sep,

doi = "10.1016/j.jfluchem.2014.05.015",

language = "English",

volume = "165",

pages = "27--32",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier B.V.",

}

TY - JOUR

T1 - 1,3-Dipolar cycloadditions of fluorinated nitrones with thioketones

AU - Mlostoń, Grzegorz

AU - Obijalska, Emilia

AU - Celeda, Małgorzata

AU - Mittermeier, Verena

AU - Linden, Anthony

AU - Heimgartner, Heinz

PY - 2014/9

Y1 - 2014/9

N2 - Fluorinated nitrones derived from fluoral and difluoroacetaldehyde react with thioketones via [3 + 2] cycloaddition yielding 1,4,2-oxathiazolidines in a regioselective manner. Unexpectedly, cycloaliphatic thioketones react faster than aromatic thioketones. Due to the presence of a fluorinated alkyl group, the cycloadducts display a remarkable stability and do not decompose at room temperature in the crystalline form nor in solution.

AB - Fluorinated nitrones derived from fluoral and difluoroacetaldehyde react with thioketones via [3 + 2] cycloaddition yielding 1,4,2-oxathiazolidines in a regioselective manner. Unexpectedly, cycloaliphatic thioketones react faster than aromatic thioketones. Due to the presence of a fluorinated alkyl group, the cycloadducts display a remarkable stability and do not decompose at room temperature in the crystalline form nor in solution.

KW - 1;3-Dipolar cycloadditions

KW - 5-Membered heterocycles

KW - Fluorinated heterocycles

KW - Nitrones

KW - Thioketones

UR - https://www.scopus.com/pages/publications/84903592988

U2 - 10.1016/j.jfluchem.2014.05.015

DO - 10.1016/j.jfluchem.2014.05.015

M3 - Article

AN - SCOPUS:84903592988

SN - 0022-1139

VL - 165

SP - 27

EP - 32

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

1,3-Dipolar cycloadditions of fluorinated nitrones with thioketones

Abstract

Keywords

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