A Sulfoximidooxirane

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-butylperoxide.

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