Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride

Romain Bejot, Steve Tisserand, L. Manmohan Ready, Deb K. Barma, Rachid Baati, J. R. Falck, Charles Mioskowski

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

(Chemical Equation Presented) Reduction of trihalomethylcarbinols 1 with CrCl2 affords good to excellent yields of (Z)-α-haloenol esters 2 and (Z)-β-haloenol ethers 3 through acyl or hydrogen migration, respectively. The reaction is proposed to proceed through regio- and stereoselective rearrangement of a chromium(III) Fischer carbene. (R2 = H, alkyl, aryl; X = F, Cl, Br).

Original languageEnglish (US)
Pages (from-to)2008-2011
Number of pages4
JournalAngewandte Chemie - International Edition
Volume44
Issue number13
DOIs
StatePublished - Mar 18 2005

Keywords

  • Carbenes
  • Chromium
  • Isotopic labeling
  • Rearrangement
  • Synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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