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Synlett 1998; 1998(1): 96-98
DOI: 10.1055/s-1998-1572
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The Preparation of (E)-1-Alkenylthiosilanes by the Reduction and Silicon Capture of 1-Alkenesulfenate Anions

Adrian L. Schwan* , Mitchell D. Refvik
  • *Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, ON, N1G2W1; Fax 1-(5 10)-7 66-14 99; E-mail: SCHWAN@CHEMBIO.UOGUELPH.CA
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Publication History

Publication Date:
31 December 2000 (online)

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A collection of (E)-1-alkenesulfenate anions were reduced by LiAlH4 at low temperature. The resulting enethiolates, with their E geometry intact, could be captured with chlorosilane to afford silicon protected enethiol ethers of thioaldehydes and thioketones. Reduction at a higher temperature prompts isomerization of the double bond.

1-alkenesulfenate - reduction - enethiolate - silyl enethiol ether - thiosilane