(2E)-N-(2-iodo-4,6-dimethylphenyl)-2-methylbut-2-enamide.
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.
Hughes
David L
DL
Wolfson Materials and Catalysis Centre, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, England.
McDermott
Michael C
MC
Stephenson
G Richard
GR
Walkington
Andrew J
AJ
D000813:Anilides / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D007536:Isomerism; D015394:Molecular Structure
D000813:Anilides; D006847:Hydrocarbons, Iodinated; C527972:N-(2-iodo-4,6-dimethylphenyl)-2-methylbut-2-enamide