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

Hughes, DL, McDermott, MC, Stephenson, GR ORCID: https://orcid.org/0000-0003-1487-9178 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
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	Rachel Smith
Date Deposited:	29 Mar 2011 11:50
Last Modified:	01 Feb 2023 10:30
URI:	https://ueaeprints.uea.ac.uk/id/eprint/27411
DOI:	10.1107/S0108270107056016

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