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Synthesis 1995; 1995(1): 47-55
DOI: 10.1055/s-1995-3860
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Preparation and Cyclopropanation of 2- and 3-Iodoalk-2-en-1-ols: Synthesis of Functionalized, Stereodefined Iodocyclopropanes

Edward Piers* , Philip D. Coish
  • *Department of Chemistry, University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada
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Publication Date:
31 December 2000 (online)

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The iodoalkenes 10-15 and 29-32 were prepared by use of a variety of synthetic methods. Cyclopropanations of these substances with the reagent derived from chloroiodomethane (ClCH2I) and diethylzinc (Et2Zn) were investigated. In the absence of ”interfering” functional groups, these reactions are clean and produce the corresponding, functionalized iodocyclopropanes in good to excellent yields.

alkenyl iodides - cyclopropanation - iodocyclopropanes - iododestannylation - modified Simmons-Smith reaction