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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 33, Number 4
BKCSDE 33(4)
April 20, 2012 

Selective Tandem Synthesis of Oximes from Benzylic Alcohols Catalyzed with 2, 3-Dichloro-5, 6-dicyanobenzoquinone
Ghasem Aghapour,* Samaneh Mohamadian
Alcohol, Oxime, 2,3-Dichloro-5,6-dicyanobenzoquinone, Tandem synthesis
In spite of many reports in the literature concerning with oxidation of benzylic alcohols to carbonyl compounds with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in stoichiometric amounts or even more, we surprisingly found that benzylic alcohols are directly oxidized to oximes using a catalytic amount of DDQ in the presence of hydroxylamine hydrochloride under solvent-free conditions. The present tandem catalytic method can be efficiently used for preparation of oximes in the presence of some other functional groups with excellent chemoselectivity.
1209 - 1212
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