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Radical translocation reactions are finding various uses in organic synthesis, in particular the stereospecific formation of complex natural products. In this work, the syntheses and single-crystal structures of two substituted 2-iodo-phenyl methyl-amides are reported, namely <i>cyclo</i>-propane carboxylic acid (2-iodo-phenyl)-methyl-amide, C₁₁H₁₂INO (<b>1</b>), and <i>cyclo</i>-heptane carboxylic acid (2-iodo-phenyl)-methyl-amide, C₁₅H₂₀INO (<b>2</b>). In each case, the methyl-amide group has a <i>syn</i> conformation, and this grouping is perpendicular to the plane of the benzene ring: these solid-state conformations appear to be well setup to allow an intramolecular hydrogen atom transfer to take place as part of a radical translocation reaction. Short intermolecular I⋯O halogen bonds occur in each crystal structure, leading to [010] chains in <b>1</b> [I⋯O = 3.012 (2) Å] and isolated dimers in <b>2</b> [I⋯O = 3.024 (4) and 3.057 (4) Å]. The intermolecular interactions are further quantified by Hirshfeld surface analyses.