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Synthesis 1994; 1994(3): 313-316
DOI: 10.1055/s-1994-25467
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Stereospecific Synthesis of Trisubstituted Alkenyl(phenyl)iodonium Salts from Vinylstannanes

Robert J. Hinkle* , Peter J. Stang
  • *Department of Chemistry, The University of Utah, Salt Lake City, Utah 84112, USA
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Publication Date:
27 September 2002 (online)

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A simple and efficient stereospecific synthesis of alkenyl(phenyl)iodonium tosylates 5a-5e and triflates 6a-6g from reaction between cyano(phenyl)iodonium tosylate (4a) or triflate (4b) and the corresponding vinylstannanes 3a-3g is described. The reaction affords 55 to 90% yields of stereodefined products with retention of the vinylstannane geometry.