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Updated: Jun 5, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
2-(4-Iodo-phen-yl)-5,7-dimethyl-3-methyl-sulfinyl-1-benzofuran
Abstract:
The title compound, C(17)H(15)IO(2)S, was prepared by the oxidation of 2-(4-iodo-phen-yl)-5,7-dimethyl-3-methyl-sulfanyl-1-benzofuran using 3-chloro-peroxy-benzoic acid. The 4-iodo-phenyl ring makes a dihedral angle of 26.0 (1)° with the plane of the benzofuran fragment, and the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of this plane. The crystal structure is stabilized by inter- and intra-molecular C-H⋯O hydrogen bonds, and by an I⋯O halogen bond with an I⋯O distance of 3.145 (2) Å and a nearly linear C-I⋯O angle of 164.01 (9)°.
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