Preparation of a Storable Zinc Carbenoid Species and Its Application in Cyclopropanation, Chain Extension, and [2, 3]-Sigmatropic Rearrangement Reactions

A Voituriez, LE Zimmer, AB Charette

Index: Voituriez, Arnaud; Zimmer, Lucie E.; Charette, Andre B. Journal of Organic Chemistry, 2010 , vol. 75, # 4 p. 1244 - 1250

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Citation Number: 29

Abstract

The formation of a new phosphate carbenoid (n-BuO) 2P (O) OZnCH2I and its application in organozinc-mediated reactions is described. This carbenoid undergoes very slow degradation in solution and can be stored for several weeks at− 20° C. Its reactivity was tested with many representative alkenes and was determined to be a powerful cyclopropanating reagent, giving the corresponding cyclopropanes in 72− 99% yield. The ...