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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


Linden, Anthony; Mloston, Grzegorz; Grzelak, Paulina; Heimgartner, Heinz (2018). 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. Acta Crystallographica. Section E: Structure Reports Online, E74:1705-1709.

Abstract

The title compounds, C19H21F3O2S and C24H19F3OS, were prepared via chemo- and regioselective [3 + 2]-cyclo-additions 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 A ̊ , 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....Pi interactions link the molecules into sheets parallel to the (010) plane.

Abstract

The title compounds, C19H21F3O2S and C24H19F3OS, were prepared via chemo- and regioselective [3 + 2]-cyclo-additions 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 A ̊ , 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....Pi interactions link the molecules into sheets parallel to the (010) plane.

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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:November 2018
Deposited On:15 Nov 2018 06:55
Last Modified:04 Dec 2018 14:50
Publisher:International Union of Crystallography
ISSN:1600-5368
OA Status:Gold
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1107/S2056989018015335
Project Information:
  • : FunderNational Science Center, Cracow, Maestro-3
  • : Grant IDDec-2012/06/A/ST5/00219
  • : Project Title

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