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Ethylenebis( N ‐Methylimidazolium) Chlorochromate (EBMICC): A New Selective and Mild Reagent for Oxidation of Alcohols, Hydroquinones and Trimethylsilyl Ethers
Author(s) -
Hosseinzadeh Rahman,
Tajbakhsh Mahmood,
Khaledi Hamid
Publication year - 2008
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200800036
Subject(s) - chemistry , acetonitrile , allylic rearrangement , reagent , trimethylsilyl , salt (chemistry) , solvent , organic chemistry , alcohol oxidation , medicinal chemistry , alcohol , catalysis
The ethylenebis( N ‐methylimidazolium) chlorochromate was prepared by addition of N ‐methylimidazole to 1,2‐dibromoethane to form the corresponding dibromide salt and subsequent treatment of this salt with CrO 3 in 6N HCl solution. It is a stable yellow‐orange solid which selectively oxidized benzylic and allylic alcohols, hydroquinones and trimethylsilyl ethers in refluxing acetonitrile. Oxidation of alcohols was also examined under solvent‐free conditions and showed much better yields of the corresponding carbonyls in a very short reaction time when compared with the conventional method.