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Strong influence of the trifluoromethyl group on the chemoselectivity of [3+2]-cycloadditions of thiocarbonyl S-methanides with α,β-unsaturated ketones


Mloston, Grzegorz; Grzelak, Paulina; Heimgartner, Heinz (2016). Strong influence of the trifluoromethyl group on the chemoselectivity of [3+2]-cycloadditions of thiocarbonyl S-methanides with α,β-unsaturated ketones. Journal of Fluorine Chemistry, 190:56-60.

Abstract

The in situ-generated reactive thiocarbonyl S-methanides were reacted with fluorinated enones. The type of the obtained [3+2]-cycloadduct depends strongly on the location of the activating CF3 group. In the case of enones containing the CF3CH=CH moiety, the [3+2]- cycloaddition occurs chemo- and regioselectively onto the C=C bond to give trifluoromethylated tetrahydrothiophene derivatives. On the other hand, enones containing the CF3–C=O unit react as carbonyl dipolarophiles leading to trifluoromethylated 1,3- oxathiolanes also in a chemo- and regioselective manner. These are the first reported reactions of thiocarbonyl S-methanides with α,β-unsaturated ketones.

Abstract

The in situ-generated reactive thiocarbonyl S-methanides were reacted with fluorinated enones. The type of the obtained [3+2]-cycloadduct depends strongly on the location of the activating CF3 group. In the case of enones containing the CF3CH=CH moiety, the [3+2]- cycloaddition occurs chemo- and regioselectively onto the C=C bond to give trifluoromethylated tetrahydrothiophene derivatives. On the other hand, enones containing the CF3–C=O unit react as carbonyl dipolarophiles leading to trifluoromethylated 1,3- oxathiolanes also in a chemo- and regioselective manner. These are the first reported reactions of thiocarbonyl S-methanides with α,β-unsaturated ketones.

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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:October 2016
Deposited On:12 Sep 2016 09:30
Last Modified:08 Dec 2017 20:22
Publisher:Elsevier
ISSN:0022-1139
Funders:National Science Center (Cracow) (Grant Opus-7 # UMO-2014/13/B/ST5/04004)
Publisher DOI:https://doi.org/10.1016/j.jfluchem.2016.08.009

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