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A mechanistic study of the chromium(II)-mediated transformations of trichloromethyl alkyls and carbinols: evidence for carbene, carbyne, and carbenoid intermediates
Authors:Romain Bejot  De Run Li  Charles Mioskowski
Affiliation:a Laboratoire de Synthèse Bio-Organique, UMR 7175-LC1, Faculté de Pharmacie, Université Louis Pasteur, 74 Route du Rhin, BP 24, 67 401 Illkirch, France
b Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, TX 75390, USA
Abstract:Using CrCl2 in THF at room temperature, trichloromethyl carbinols and trichloromethylalkanes are readily transformed to the highly reactive α-chlorocarbenes, carbynes and α-chloro-α-chromium(III) vinylidene carbenoids. A mechanistic study is carried out to determine the nature of the intermediates.
Keywords:Carbene   Carbyne   Chromium   Isotopic labeling   Rearrangement
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