Bulletin of the Korean Chemical Society

  • 제26권8호
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  • Pages.1190-1196
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  • 2005
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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The Mechanisms for Thermal and Photochemical Isomerizations of N-Substituted 2-Halopyrroles: Syntheses of N-Substituted 3-Halopyrroles

  • 발행 : 2005.08.20
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초록

Halopyrroles, N-substituted 2-halopyrroles were prepared by halogenation of N-substituted pyrroles with NBS, NCS, or surfuryl chloride. N-Substituted 3-halopyrroles were synthesized by acid-catalyzed thermal and photochemical isomerization reactions of N-substituted 2-halopyrroles. Both the thermal and photochemical reactions were acid-catalyzed. For the acid-catalyzed isomerization, a mechanism of [1,3] bromine shift followed by deprotonation is operated. For the acid-catalyzed photoisomerization, an excited triplet state of 2-protonated N-benzyl-2-halopyrrole produces an intermediate N-substituted pyrrole complex with halonium ion which is equilibrated with N-substituted pyrrole plus halonium ion, and then the halonium ion newly adds to 3-position of N-substituted pyrrole followed by deprotonation to afford N-benzyl-3-halopyrrole.

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참고문헌

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피인용 문헌

  1. Ozone-Activated Halogenation of Mono- and Dimethylbipyrrole in Seawater vol.51, pp.1, 2017, https://doi.org/10.1021/acs.est.6b03601
  2. Acid catalyzed halogen dance on deactivated pyrroles pp.19435193, 2010, https://doi.org/10.1002/jhet.276