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 journalArticle

31 Citations (Scopus)

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

Fingerprint

Ethers
Chromium
Hydrogen
Esters
chromous chloride
carbene

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride. / Bejot, Romain; Tisserand, Steve; Ready, L. Manmohan; Barma, Deb K.; Baati, Rachid; Falck, J. R.; Mioskowski, Charles.

In: Angewandte Chemie - International Edition, Vol. 44, No. 13, 18.03.2005, p. 2008-2011.

Research output: Contribution to journalArticle

Bejot, Romain ; Tisserand, Steve ; Ready, L. Manmohan ; Barma, Deb K. ; Baati, Rachid ; Falck, J. R. ; Mioskowski, Charles. / Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride. In: Angewandte Chemie - International Edition. 2005 ; Vol. 44, No. 13. pp. 2008-2011.
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