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http://dx.doi.org/10.5012/bkcs.2002.23.9.1208

Photoinduced Intramolecular Substitution Reaction of Aryl Halide with Carbonyl Oxygen of Anide Group  

Park, Yeong-Tae
Song, Myong-Geun
Kim, Moon-Sub
Kwon, Jeong-Hee
Publication Information
Bulletin of the Korean Chemical Society / v.23, no.9, 2002 , pp. 1208-1254 More about this Journal
Abstract
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.
Keywords
N-(o-Hanlphenyl)acetamide; N-(o-Haloenzyl)acetamide; Intramolecular photosubstitution; Photoreduction; Methylbenzoxazole;
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Times Cited By Web Of Science : 7  (Related Records In Web of Science)
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