Object's details: Chemo- and regioselective [3 + 2]-cycloadditions of thiocarbonyl ylides: crystal structures of trans-8-benzoyl-1,1,3,3-tetramethyl-7-trifluoromethyl-5-thiaspiro[3.4]octan-2-one and trans-3-benzoyl-2,2-diphenyl-4-(trifluoromethyl)tetrahydrothiophene

Provider:Repozytorium Uniwersytetu Łódzkiego

Description

Title:
Chemo- and regioselective [3 + 2]-cycloadditions of thiocarbonyl ylides: crystal structures of trans-8-benzoyl-1,1,3,3-tetramethyl-7-trifluoromethyl-5-thiaspiro[3.4]octan-2-one and trans-3-benzoyl-2,2-diphenyl-4-(trifluoromethyl)tetrahydrothiophene
Creator:
Mlostoń, Grzegorz;
Grzelak, Paulina;
Linden, Anthony;
Heimgartner, Heinz
Contributor:
Department of Organic and Applied Chemistry, University of Łódź, Tamka 12, PL-91-403 Łódź, Poland;
Department of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland;
anthony.linden@chem.uzh.ch
Description:
The title compounds, C19H21F3O2S and C24H19F3OS, were prepared via chemo- and regioselective [3 + 2]-cycloadditions of the respective thiocarbonyl ylides (thiocarbonyl S-methanides), generated in situ, with (E)-4,4,4-trifluoro-1-phenylbut-2-en-1-one. The thiophene ring in the crystal structure of each compound has an envelope conformation. The largest differences between the two molecular structures is in the bond lengths about the quaternary C atom of the thiophene ring; in the spirocyclic structure, the C—C bonds to the spiro C atom in the cyclobutane ring are around 1.60 Å, although this is also observed in related structures. In the same structure, weak intermolecular C—H⋯X (X = S, O) interactions link the molecules into extended ribbons running parallel to the [001] direction. In the other structure, weak C—H⋯π interactions link the molecules into sheets parallel to the (010) plane.;
Funding for this research was provided by: Maestro-3, National Science Center, Cracow (grant No. Dec-2012/06/A/ST5/00219 to GM).
Object availability:
free access
Rights:
Uznanie autorstwa 4.0 Międzynarodowe;
http://creativecommons.org/licenses/by/4.0
Date:
2022.01.31;
2018
Type:
Article
Language:
English
Format:
application/pdf
Publisher:
International Union of Crystallography
Relation:
Acta Crystallographica Section E: Crystallographic Communications;74;
12
Subject:
crystal structure;
tetrahydrothiophene;
[3 + 2]-cycloaddition
Identifier:
2056-9890;
http://hdl.handle.net/11089/40539 ;
10.1107/S2056989018015335
Data provider:
Repozytorium Uniwersytetu Łódzkiego

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Object's details: Chemo- and regioselective [3 + 2]-cyclo­additions of thio­carbonyl ylides: crystal structures of trans-8-benzoyl-1,1,3,3-tetra­methyl-7-tri­fluoro­methyl-5-thia­spiro­[3.4]octan-2-one and trans-3-benzoyl-2,2-di­phenyl-4-(tri­fluoro­meth­yl)tetra­hydro­thio­phene

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