Journal of Photoscience

한국광과학회 (Korean Society of Photoscience)
권호 표지

Photoreaction of N-(2-Halophenyl)cyclohexanecarboxamide:Synthesis of 2-Alkylbenzoxazole

  • Park, Yong-Tae (Department of Chemistry, Kyungpook National University) ;
  • Kim, Moon-Sub (Department of Chemistry, Kyungpook National University) ;
  • Kwak, Young-Woo (Department of Chemistry, Kyungpook National University) ;
  • Lee, Jae-Keun (Department of Chemistry, Kyungpook National University) ;
  • Yoh, Soo-Dong (Department of Chemistry, Kyungpook National University) ;
  • Kim, Woo-Sik (Department of Polymer Science,Kyungpook National University)
  • 발행 : 2000.12.01
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초록

The photochemical behavior of haloarene tethered to alkyl by an amide bone(1,2) was studied. The photoreaction of N-(2-bromophenyl) cyclohexanecarboxamide (1b) in basic medium afforded intramolecular substitute product, 2-cyclohexylbenzoxazole (4) and reduced product, N-phenylcyclohexanecarboxamide (5)in 33 and 26% yield, respectively. The chloro analogue(1a) produced photo-Fries type and photosubstituted products(6,4), whereas the iodo analogue produced extensively photoreduced product 5. N-(2-bromophenyl)-N-methylcyclohexanecarboxamide (2), which can not exist as imidol form, produced a photocyclized product, supporting as imidol form is involved in the intramolecular photosubstitution. since the photoreduction but the photosubstitution reaction is retarded by the presence of oxygen, a trilpet state for the photoreduction and a singlet state for the photosubstitution are involved.

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참고문헌

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