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Phase Transfer Oxidations with Hypochlorite: Scope and Mechanism
Author(s) -
Lee George A.,
Freedman H.H.
Publication year - 1985
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198500100
Subject(s) - chemistry , hypochlorite , catalysis , phase transfer catalyst , sodium hypochlorite , scope (computer science) , organic chemistry , solvent , ammonium , salt (chemistry) , aqueous medium , combinatorial chemistry , aqueous solution , computer science , programming language
The use of phase transfer catalysis (PTC), with catalytic amounts of lipophilic quaternary ammonium salts for the transfer of hypochlorite ion from aqueous to organic media, has been found to be an extremely effective and convenient method for the oxidation of many alcohols and amines. An interesting and unexpected specific solvent effect has also been discovered with the use of ethyl acetate which greatly expands the synthetic utility of this method. Both the synthetic scope and mechanistic aspects of these reactions are reported.