Related Experiment Video
Updated: May 10, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
2-Tosyl-2,3,3a,4,9,9a-hexa-hydro-1H-benzo[f]isoindol-1-one
1School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, People's Republic of China.
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⋯π inter-actions leads to inversion dimers.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
Related Concept Videos
Nomenclature of Aromatic Compounds with Multiple Substituents
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
Nomenclature of Aromatic Compounds with a Single Substituent
Five-Membered Heterocyclic Aromatic Compounds: Overview
Reactions at the Benzylic Position: Oxidation and Reduction
Reactions at the Benzylic Position: Halogenation
NMR Spectroscopy of Benzene Derivatives