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Synlett 1992; 1992(3): 197-198
DOI: 10.1055/s-1992-21311
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Substitution-Desulphurisation Chemistry of a Thiane Oxide System

Paul J. Cox* , Andrew Persad, Nigel S. Simpkins
  • *Department of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, England
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Publication Date:
08 March 2002 (online)

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The chemistry of trans-4-tert-butyl(diphenyl)-siloxythiane oxide (1) has been explored as a means of obtaining substituted secondary alcohols in protected form. For example, the anion of compound 1 was treated with trimethylsilyl chloride to give the 2,4-disubstituted thiane 3. Desulphurisation with Raney nickel gave (S)-3-tert-butyl (diphenyl)siloxy-1-trimethyl-silylpentane (18).

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