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Synthesis 1996; 1996(5): 637-640
DOI: 10.1055/s-1996-4268
DOI: 10.1055/s-1996-4268
paper
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Selective Synthesis of cis-α,β-Unsaturated Sulfoxides and Sulfides by the Horner-Wittig Reaction with Bis(2,2,2-trifluoroethyl)phosphono Sulfoxides and Aromatic Aldehydes
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Publication History
Publication Date:
31 December 2000 (online)
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cis-α,β-Unsaturated sulfoxides were predominantly formed in the Horner-Wittig reaction with bis(2,2,2-trifluoroethyl)phosphono sulfoxides and aromatic aldehydes, while the reaction of the corresponding sulfides showed trans- or lower cis-selectivity. The reduction of cis-α,β-unsaturated sulfoxides with tributylphosphine in carbon tetrachloride gave cis-vinyl sulfides with retention of stereochemistry.
Horner-Wittig reaction - bis(trifluoroethyl)phosphono sulfoxide - cis-selectivity - cis-α,β-unsaturated sulfoxide - cis-vinyl sulfide