1020 J. Chin. Chem. Soc., Vol. 52, No. 5, 2005
Khazaei and Amini Manesh
the reaction occurs at room temperature; there is no forma-
tion of over oxidation products due to high chemoselectivity;
and mild nature of the DCDMH. The OH and C=C functional
groups in the oxime structure do not get oxidized to other
functional groups; there is an easy work-up procedure, good
yields and finally, the dechlorinated product 2 can be con-
verted to 1 and reused several times.
Council for partial support of this work.
Received January 18, 2005.
REFERENCES
The proposed mechanism for deoximation by title re-
agent is shown in Scheme V.15
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EXPERIMENTAL SECTION
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GENERAL PROCEDURE FOR DEOXIMATION
A mixture of the oxime (3 mmol) and 1,3-dichloro-
5,5-dimethyl hydantoin 1, (3 mmol, 591.07 mg) in acetonea
(10 mL) and water (0.1 mL) was stirred at the temperature as
indicated in Table 1 for the specified time. After the reaction
was completed (TLC), the solvent was removed under re-
duced pressure, and CH2Cl2 or CCl4* (10 mL) was added to
the mixture; it was stirred for 10 minutes, then the 5,5-di-
methyl hydantoin (2) was removed by filtration and the prod-
uct was purified by column chromatography (hexane/diethyl
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* [For benzoin oxime; after the reaction was completed,
the solvent was removed under reduced pressure, and product
was purified by column chromatography (hexane/Et2O].
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a
CH2Cl2 was used for isobutyraldehyde, and ethyl
methyl ketone.
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ACKNOWLEDGEMENT
We are grateful to Bu-Ali Sina University Research