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Lookup NU author(s): Emeritus Professor Bill Clegg,
Dr Mark Elsegood,
Professor Richard Jackson
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The crystal structure of the title compound, S-(trans-3-methyl-2-oxiranyl)-S-phenyl-N-(p-tolylsulfonyl)sulfoximide, C16H17NO4S2, has two independent molecules in the asymmetric unit, which differ significantly only in the conformation of the (p-tolylsulfonyl)sulfoximide group. The powerful electron-withdrawing properties of the sulfoximide substituent produce a marked difference in the C - O bond lengths of the oxirane ring, the nearer bond being substantially shortened relative to the distal bond. The observed structure further demonstrates the high degree of diastereoselectivity in the nucleophilic epoxidation of vinylsulfoximides with lithium tert-buty]-peroxide.
Author(s): Clegg W, Elsegood MRJ, Jackson RFW, Bailey PL, Briggs AD
Publication type: Article
Publication status: Published
Journal: Acta Crystallographica Section C: Crystal Structure Communications
Print publication date: 15/11/1996
ISSN (print): 0108-2701
ISSN (electronic): 1600-5759
Publisher: Wiley-Blackwell Publishing