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Synthesis 1988; 1988(1): 56-58
DOI: 10.1055/s-1988-27463
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Cleavage of Tetrahydrofuran by tert-Butyldimethylsilyl Iodide and Further Transformations of the Resulting 1-Silyloxy-4-Iodobutane

Jan-Erik Nyström* , Terrence D. Mccanna, Paul Helquist, Roger Amouroux
  • *Department of Organic Chemistry, Royal Institute of Technology, S-100 44 Stockholm, Sweden, and Department of Chemistry, University of Notre Dame, Notre Dame, IN 46556, USA
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Publication History

Publication Date:
12 September 2002 (online)

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Tetrahydrofuran is readily cleaved by tert-butyldimethylsilyl iodide generated in situ by reaction of the chloride with sodium iodide in acetonitrile to give the corresponding 1-silyloxy-4-iodobutane, which in turn undergoes a number of useful functionalizations of the iodo group including substitutions with hetero nucleophiles, such as amine, thiolate, sulfinate, and phosphite and carbon nucloephiles such as enolate and acetylide, with survival of the silyloxy group.

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