Related Experiment Video
Updated: Jun 1, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
5-(4-Bromo-phen-yl)-2-(3,4-methyl-ene-dioxy-phen-yl)-3-methyl-sulfanyl-1-benzofuran
Abstract:
The title compound, C(22)H(15)BrO(3)S, crystallizes with four mol-ecules in the asymmetric unit. The 4-bromo-phenyl rings are rotated out of the benzofuran planes, with dihedral angles for the four mol-ecules of 20.8 (2), 17.8 (2), 23.5 (4) and 23.9 (4)°. The dihedral angles between the 3,4-methyl-ene-dioxy-phenyl ring and the benzofuran plane are 13.5 (2), 7.1 (2), 18.6 (3) and 14.2 (3)° in the four mol-ecules. The crystal structure is stabilized by weak nonclassical inter-molecular C-H⋯O hydrogen bonds. The crystal structure also exhibits inter-molecular aromatic π-π inter-actions between the benzene and furan rings and between the 4-bromo-phenyl and 3,4-methyl-enedioxy-phenyl rings from mol-ecules of the same type; the centroid-centroid distances are 3.92 (1) and 3.79 (1), 3.91 (1), 3.77 (1) and 3.77 (1), and 3.79 (1) and 3.75 (1)Å in the four mol-ecules.
Related Concept Videos
NMR Spectroscopy of Benzene Derivatives
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Preparation and Reactions of Sulfides
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

