Thianickelacycles by Ring-Opening Reactions of Cyclic Thioethers and Their Subsequent Carbonylation to Thioesters

Authors

  • Dr. Phillip T. Matsunaga,

    1. Searle Chemistry Laboratory, Department of Chemistry, The University of Chicago, 5735 S. Ellis Avenue, Chicago, IL 60637 (USA), Telefax: Int. code + (312) 702-0805
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  • Prof. Gregory L. Hillhouse

    Corresponding author
    1. Searle Chemistry Laboratory, Department of Chemistry, The University of Chicago, 5735 S. Ellis Avenue, Chicago, IL 60637 (USA), Telefax: Int. code + (312) 702-0805
    • Searle Chemistry Laboratory, Department of Chemistry, The University of Chicago, 5735 S. Ellis Avenue, Chicago, IL 60637 (USA), Telefax: Int. code + (312) 702-0805
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  • This work was supported by a U. S. National Science Foundation grant (CHE-9200943 to G. L. H.).

Abstract

original image

A functional model for the nickel-containing CO-dehydrogenase? Oxidative addition reactions of ethylene sulfide, propylene sulfide, and thietane with nickel complexes like 1 yield thianickelacycles. Formally analogous to the biosynthesis of acetyl coenzyme A, 2 undergoes an insertion reaction with CO followed by reductive elimination of the thiobutyrolactone 3.

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