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Synlett 1997; 1997(10): 1165-1166
DOI: 10.1055/s-1997-987
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A New Tin Mediated Pummerer Synthesis of Vinyl Stannanes

Ian A. O'Neil* , J. Mike Southern
  • *Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Crown St, P.O.Box 147, Liverpool L69 7ZD, U.K.
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Publication Date:
31 December 2000 (online)

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Treatment of a range of sulfoxides with 3 equivalents of LDA and 6 equivalents of tri-n-butyltin chloride yields the corresponding α-tributylstannyl vinyl sulfides in good yield. When a tert-butyl sulfoxide is used the α-tributylstannyl vinyl sulfide is isolated as a single geometric isomer.

Pummerer - vinyl stannane - sulfoxide