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1,3-Dipolar cycloadditions of fluorinated nitrones with thioketones


Mloston, Grzegorz; Obijalska, Emilia; Celeda, Malgorzata; Mittermeier, Verena; Linden, Anthony; Heimgartner, Heinz (2014). 1,3-Dipolar cycloadditions of fluorinated nitrones with thioketones. Journal of Fluorine Chemistry, 165:27-32.

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.

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2014
Deposited On:02 Jul 2014 15:34
Last Modified:05 Apr 2016 17:56
Publisher:Elsevier
ISSN:0022-1139
Funders:National Science Center (PL-Cracow) (Grant Maestro-3 (Dec-2012/ 06/A/ST5/00219))
Publisher DOI:https://doi.org/10.1016/j.jfluchem.2014.05.015

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