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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 27, Number 12
BKCSDE 27(12)
December 20, 2006 

Oxidation of Dibenzyl Sulfide via an Oxygen Transfer from Palladium Nitrate
Young-ae Whang Park, Yongho Na, Du-Jong Baek*
Dibenzyl sulfide, Palladium nitrate, Benzaldehyde, Oxidation
Dibenzyl sulfide was oxidized at the α-carbon to yield benzaldehyde in the presence of Pd(NO3)2. Oxygen itself could not oxidize the sulfide directly, instead the nitrato ligand of the palladium complex transferred oxygen to dibenzyl sulfide to form benzaldehyde. The X-ray crystal structure of the intermediate complex, cis- [Pd(NO3)2{S(CH2C6H5)2}2], revealed that the nitrato ligand was unidentate. Para-substituted dibenzyl sulfides I, (YC6H4CH2)2S wherein Y = OCH3, CH3, Cl, CN, or NO2, were synthesized and reacted with palladium nitrate, and those with electron-donating substituents (Y = OCH3 and CH3) were good substrates for the oxidation reaction with palladium nitrate. Thus, the reaction mechanism of the oxygen transfer was proposed to include nucleophilic benzylic carbon.
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