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Issue 5, 1993
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Diastereoselective synthesis of cyclopropanes with multiple sulfur substitution. X-Ray molecular structures of phenylsulfonyl-substituted cyclopropanes

Abstract

Reaction of 1-phenylsulfonyl-1-phenylthioalkenes 3 with lithiated phenyl phenylthiomethyl sulfone 4 gave 1-phenylsulfonyl-1, 2-bis(phenylthio)cyclopropanes 5 as single diastereoisomers in good yield. The relative stereochemistry of the cyclopropane 5a was established by an X-ray crystal-structure determination. Oxidation of the cyclopropane 5a with m-chloroperbenzoic acid gave the tris-sulfone 6 which, either on heating or on treatment with base, was converted efficiently into the epimeric tris-sulfone 7. The structures of both of these sulfones were established by X-ray crystal-structure determinations. Reaction of lithiated phenyl phenylthiomethyl sulfone with the 1-(phenylthio)vinylsulfoximide 9 gave the cyclopropanes 11a and 11b as a 3:1 mixture of diastereoisomers. The structure of the major product 11a was established by an X-ray crystal-structure determination. Reaction of lithiated phenyl phenylthiomethyl sulfone with the simple vinylsulfoximide 10b gave the 1-phenylsulfonyl-1-phenylthiocyclopropane 12 in moderate yield, and the structure was determined by X-ray crystallography. The structural parameters of the cyclopropanes are compared, and asymmetry parameters are reported.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1993, 577-584
Article type
Paper

Diastereoselective synthesis of cyclopropanes with multiple sulfur substitution. X-Ray molecular structures of phenylsulfonyl-substituted cyclopropanes

P. L. Bailey, C. T. Hewkin, W. Clegg and R. F. W. Jackson, J. Chem. Soc., Perkin Trans. 1, 1993, 577
DOI: 10.1039/P19930000577

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