Stereoselective Transformations of Trihalomethylcarbinols Induced by Chromous Chloride | Zendy

Bejot Romain | Zendy; Tisserand Steve | Zendy; Reddy L. Manmohan | Zendy; Barma Deb K. | Zendy; Baati Rachid | Zendy; Falck J. R. | Zendy; Mioskowski Charles | Zendy

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Stereoselective Transformations of Trihalomethylcarbinols Induced by Chromous Chloride

Author(s) -

Bejot Romain,

Tisserand Steve,

Reddy L. Manmohan,

Barma Deb K.,

Baati Rachid,

Falck J. R.,

Mioskowski Charles

Publication year - 2005

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200461884

Subject(s) - stereoselectivity , carbene , chromium , alkyl , chemistry , aryl , reduction (mathematics) , chloride , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , mathematics , geometry

Reduction of trihalomethylcarbinols 1 with CrCl 2 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. (R 2 =H, alkyl, aryl; X=F, Cl, Br).

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