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Efficient synthesis of fluoroalkylated 1,4,2-oxathiazoles via regioselective [3 + 2]-cycloaddition of fluorinated nitrile oxides with thioketones


Mloston, Grzegorz; Kowalski, Marcin K; Obijalska, Emilia; Heimgartner, Heinz (2017). Efficient synthesis of fluoroalkylated 1,4,2-oxathiazoles via regioselective [3 + 2]-cycloaddition of fluorinated nitrile oxides with thioketones. Journal of Fluorine Chemistry, 199:92-96.

Abstract

Fluorinated acetonitrile oxides, generated from the corresponding hydroximoyl bromides in the presence of aryl, hetaryl, ferrocenyl, and cycloaliphatic thioketones, undergo efficient [3 + 2]-cycloadditions to give 3- fluoroalkylated 1,4,2-oxathiazoles in good to excellent yields. The reactions proceed regioselectively with no competitive formation of furoxans as dimers of the intermediate 1,3-dipoles.

Abstract

Fluorinated acetonitrile oxides, generated from the corresponding hydroximoyl bromides in the presence of aryl, hetaryl, ferrocenyl, and cycloaliphatic thioketones, undergo efficient [3 + 2]-cycloadditions to give 3- fluoroalkylated 1,4,2-oxathiazoles in good to excellent yields. The reactions proceed regioselectively with no competitive formation of furoxans as dimers of the intermediate 1,3-dipoles.

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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:May 2017
Deposited On:17 May 2017 08:53
Last Modified:04 Jun 2017 18:55
Publisher:Elsevier
ISSN:0022-1139
Funders:National Science Center (Cracow, Poland) OPUS-7 grant (project number 2014/13/B/ST5/04004), National Science Center (Cracow, Poland) Maestro- 3 grant (project number 2012/06A/ST5/00219)
Publisher DOI:https://doi.org/10.1016/j.jfluchem.2017.04.011

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Embargo till: 2019-07-31

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