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

ABSTRACT: The title compound, C19H19NO3S, was produced by the self-reaction of N-cinnamyl-N-tosyl-acryl-amide in the presence of palladium(II) acetate via an intra-molecular C-C coupling reaction and C-H activation. There are two chiral C atoms in the mol-ecule, but the crystal is a racemic system due to a lack of chiral separation. The five-membered ring is twisted about the methyl-ene-methane bond, and the cyclo-hexa-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 mol-ecule. In the crystal, the presence of C-H?? inter-actions leads to inversion dimers.

SUBMITTER: Wu M

PROVIDER: S-EPMC3685075 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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

Wu Min M Hu Yi-Min YM

Acta crystallographica. Section E, Structure reports online 20130518 Pt 6

The title compound, C19H19NO3S, was produced by the self-reaction of N-cinnamyl-N-tosyl-acryl-amide in the presence of palladium(II) acetate via an intra-molecular C-C coupling reaction and C-H activation. There are two chiral C atoms in the mol-ecule, but the crystal is a racemic system due to a lack of chiral separation. The five-membered ring is twisted about the methyl-ene-methane bond, and the cyclo-hexa-1,4-diene ring has a boat conformation. The dihedral angle between the benzene rings is ...[more]

PMID: 23795094

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