Convenient synthesis of (e)-5-aryl(halo)methylenebicyclo-[2.2.2]oct-2-enes and -[2.2.1]hept-2-enes via Lewis acid-promoted carbohalogenation of cyclic 2,6-enynols

Ming Chang P. Yeh, Hsin Hui Lin, Siou Fu Kuo, Pei Jie Chen, Jyun Wei Honga

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

An efficient synthesis of (E)-5-aryl(halo)-methylenebicyclo[2.2.2]oct-2-enes is reported. Lewis acid-promoted carbohalogenation of 4-(3-arylprop-2-ynyl)-cyclohex-2-enols in dichloromethane proceeds rapidly to afford the exo-methylenebridged bicycles in good yields. This method also provides an easy access to (E)-5-aryl(halo)methyl-ACHTUNGTRENUNGenebicyclo[2.2.1]hept-2-enes from the five-membered ring 2,6-enynols. The reactions are procedurally simple and high yielding, producing the aryl(halo) methylene-bridged bicycles in minutes under air and mild conditions.

Original languageEnglish
Pages (from-to)3816-3820
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number18
DOIs
Publication statusPublished - 2014 Dec 15

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Lewis Acids
Bicycles
Acids
Methylene Chloride
Dichloromethane
Air

Keywords

  • Carbocations
  • Carbocycles
  • Cyclization
  • Enynes
  • Halogenation
  • Lewis acids

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Convenient synthesis of (e)-5-aryl(halo)methylenebicyclo-[2.2.2]oct-2-enes and -[2.2.1]hept-2-enes via Lewis acid-promoted carbohalogenation of cyclic 2,6-enynols. / Yeh, Ming Chang P.; Lin, Hsin Hui; Kuo, Siou Fu; Chen, Pei Jie; Honga, Jyun Wei.

In: Advanced Synthesis and Catalysis, Vol. 356, No. 18, 15.12.2014, p. 3816-3820.

Research output: Contribution to journalArticle

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abstract = "An efficient synthesis of (E)-5-aryl(halo)-methylenebicyclo[2.2.2]oct-2-enes is reported. Lewis acid-promoted carbohalogenation of 4-(3-arylprop-2-ynyl)-cyclohex-2-enols in dichloromethane proceeds rapidly to afford the exo-methylenebridged bicycles in good yields. This method also provides an easy access to (E)-5-aryl(halo)methyl-ACHTUNGTRENUNGenebicyclo[2.2.1]hept-2-enes from the five-membered ring 2,6-enynols. The reactions are procedurally simple and high yielding, producing the aryl(halo) methylene-bridged bicycles in minutes under air and mild conditions.",
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