title: (2E)-N-(2-iodo-4,6-dimethylphenyl)-2-methylbut-2-enamide.
abstract: The title compound, C14H18INO, crystallizes as +sc/+sp/+sc 2-iodoanilide molecules (and racemic opposites) and shows significant intermolecular I...O interactions in the solid state, forming dimeric pairs about centres of symmetry. Under asymmetric Heck conditions, the S enantiomer of the dihydroindol-2-one was obtained using (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl [(R)-BINAP], suggesting a mechanism that proceeds by oxidative addition to give the title (P) enantiomer of the compound and pro-S coordination of the Re face of the alkene in a conformation similar to that defined crystallographically, except that rotation about the C-C bond of the butenyl group is required.
authors.affiliation: Wolfson Materials and Catalysis Centre, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, England.
authors.forename: David L
authors.initials: DL
authors.lastname: Hughes
authors.forename: Michael C
authors.initials: MC
authors.lastname: McDermott
authors.forename: G Richard
authors.initials: GR
authors.lastname: Stephenson
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Walkington
mesh_terms: D000813:Anilides / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007536:Isomerism; D015394:Molecular Structure
chemical_list: D000813:Anilides; D006847:Hydrocarbons, Iodinated; C527972:N-(2-iodo-4,6-dimethylphenyl)-2-methylbut-2-enamide