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A sulfoximidooxirane

Lookup NU author(s): Emeritus Professor Bill CleggORCiD, 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.

Publication metadata

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

Year: 1996

Volume: 52

Issue: 11

Pages: 2781-2783

Print publication date: 15/11/1996

ISSN (print): 0108-2701

ISSN (electronic): 1600-5759

Publisher: Wiley-Blackwell Publishing