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2-Tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-benzo[f]isoindol-1-one

The title compound, C(19)H(19)NO(3)S, was produced by the self-reaction of N-cinnamyl-N-tosyl­acryl­amide in the presence of palladium(II) acetate via an intra­molecular C—C coupling reaction and C—H activation. There are two chiral C atoms in the mol­ecule, but the crystal is a racemic system due t...

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Detalles Bibliográficos
Autores principales: Wu, Min, Hu, Yi-Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685075/
https://www.ncbi.nlm.nih.gov/pubmed/23795094
http://dx.doi.org/10.1107/S1600536813011045
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author Wu, Min
Hu, Yi-Min
author_facet Wu, Min
Hu, Yi-Min
author_sort Wu, Min
collection PubMed
description The title compound, C(19)H(19)NO(3)S, was produced by the self-reaction of N-cinnamyl-N-tosyl­acryl­amide in the presence of palladium(II) acetate via an intra­molecular C—C coupling reaction and C—H activation. There are two chiral C atoms in the mol­ecule, but the crystal is a racemic system due to a lack of chiral separation. The five-membered ring is twisted about the methyl­ene–methane bond, and the cyclo­hexa-1,4-diene ring has a boat conformation. The dihedral angle between the benzene rings is 88.27 (14)°, indicating an almost orthogonal relationship and an approximate L-shape for the mol­ecule. In the crystal, the presence of C—H⋯π inter­actions leads to inversion dimers.
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spelling pubmed-36850752013-06-21 2-Tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-benzo[f]isoindol-1-one Wu, Min Hu, Yi-Min Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(19)NO(3)S, was produced by the self-reaction of N-cinnamyl-N-tosyl­acryl­amide in the presence of palladium(II) acetate via an intra­molecular C—C coupling reaction and C—H activation. There are two chiral C atoms in the mol­ecule, but the crystal is a racemic system due to a lack of chiral separation. The five-membered ring is twisted about the methyl­ene–methane bond, and the cyclo­hexa-1,4-diene ring has a boat conformation. The dihedral angle between the benzene rings is 88.27 (14)°, indicating an almost orthogonal relationship and an approximate L-shape for the mol­ecule. In the crystal, the presence of C—H⋯π inter­actions leads to inversion dimers. International Union of Crystallography 2013-05-18 /pmc/articles/PMC3685075/ /pubmed/23795094 http://dx.doi.org/10.1107/S1600536813011045 Text en © Wu and Hu 2013 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Wu, Min
Hu, Yi-Min
2-Tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-benzo[f]isoindol-1-one
title 2-Tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-benzo[f]isoindol-1-one
title_full 2-Tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-benzo[f]isoindol-1-one
title_fullStr 2-Tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-benzo[f]isoindol-1-one
title_full_unstemmed 2-Tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-benzo[f]isoindol-1-one
title_short 2-Tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-benzo[f]isoindol-1-one
title_sort 2-tosyl-2,3,3a,4,9,9a-hexa­hydro-1h-benzo[f]isoindol-1-one
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685075/
https://www.ncbi.nlm.nih.gov/pubmed/23795094
http://dx.doi.org/10.1107/S1600536813011045
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