Abstract
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 cyclo-propane carboxylic acid (2-iodo-phenyl)-methyl-amide, C11H12INO (1), and cyclo-heptane carboxylic acid (2-iodo-phenyl)-methyl-amide, C15H20INO (2). In each case, the methyl-amide group has a syn 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 1 [I⋯O = 3.012 (2) Å] and isolated dimers in 2 [I⋯O = 3.024 (4) and 3.057 (4) Å]. The intermolecular interactions are further quantified by Hirshfeld surface analyses.
Original language | English |
---|---|
Pages (from-to) | 1233–1242 |
Number of pages | 10 |
Journal | Chemistry |
Volume | 5 |
Issue number | 2 |
Early online date | 12 May 2023 |
DOIs | |
Publication status | Published - 12 May 2023 |
Bibliographical note
AcknowledgmentsWe thank the EPSRC National Crystallography Service (University of Southampton, England) for the X-ray data collection for 2.
Funding
This research received no external funding.
Keywords
- methyl-amides
- halogen bonds
- conformational analysis