(2E)-N-(2-Iodo-4,6-dimethylphenyl)-2-methylbut-2-enamide

Hughes, DL, McDermott, MC, Stephenson, GR and Walkington, AJ (2007) (2E)-N-(2-Iodo-4,6-dimethylphenyl)-2-methylbut-2-enamide. Acta Crystallographica Section C: Crystal Structure Communications, 64 (1). o7-o9. ISSN 0108-2701

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Abstract

The title compound, C14H18INO, crystallizes as +sc/+sp/+sc 2-iodoanilide molecules (and racemic opposites) and shows significant intermolecular I center dot center dot center dot 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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
Related URLs:
Depositing User: Rachel Smith
Date Deposited: 29 Mar 2011 11:50
Last Modified: 28 Oct 2019 15:41
URI: https://ueaeprints.uea.ac.uk/id/eprint/27411
DOI: 10.1107/S0108270107056016

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