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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 23, Number 9
BKCSDE 23(9)
September 20, 2002 

Photoinduced Intramolecular Substitution Reaction of Aryl Halide with Carbonyl Oxygen of Amide Group
Yong-Tae Park, Myong-Geun Song, Moon-Sub Kim, Jeong-Hee Kwon
N-(o-Halophenyl)acetamide, N-(o-Halobenzyl)acetamide, Intramolecular photosubstitution, Photoreduction, Methylbenzoxazole
Photoreaction of N-(o-halophenyl)acetamide in basic acetonitrile produces an intramolecular substituted product, 2-methylbenzoxazole in addition to reduced product, acetanilide, whereas photoreaction of N-(o-halobenzyl) acetamide affords a reduced product, N-benzylacetamide only. On the basis of preparative reaction, kinetics, and UV/vis absorption behavior, an electrophilic aromatic substitution of aryl halide with oxygen of its amide bond are proposed.
1208 - 1212
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