Bulletin of the Korean Chemical Society

  • 제23권9호
  • /
  • Pages.1208-1254
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  • 2002
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Photoinduced Intramolecular Substitution Reaction of Aryl Halide with Carbonyl Oxygen of Anide Group

  • 발행 : 2002.09.20
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초록

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.

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참고문헌

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  9. Photo-Fries type product was identified by GC/Mass. The regiochemistry of acetyl group on chloroaniline (between o-and p-and position)is not determined

피인용 문헌

  1. A Domino Copper-Catalyzed CN and CO Cross-Coupling for the Conversion of Primary Amides into Benzoxazoles vol.346, pp.13-15, 2004, https://doi.org/10.1002/adsc.200404182
  2. -Monomethylation of Primary Aryl Amines vol.27, pp.7, 2009, https://doi.org/10.1002/cjoc.200990224
  3. Photoinduced Intramolecular Substitution Reaction of Aryl Halide with Carbonyl Oxygen of Amide Group. vol.34, pp.8, 2002, https://doi.org/10.1002/chin.200308047
  4. Substituent Effect in Photochemistry of Carbonyl Compounds: α-Halovalerophenones vol.25, pp.1, 2004, https://doi.org/10.5012/bkcs.2004.25.1.042