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

doi:10.1002/adsc.201400671

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

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

10 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 language	English
Pages (from-to)	3816-3820
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	356
Issue number	18
DOIs	https://doi.org/10.1002/adsc.201400671
Publication status	Published - 2014 Dec 15

Keywords

Carbocations
Carbocycles
Cyclization
Enynes
Halogenation
Lewis acids

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201400671

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

Research output: Contribution to journal › Article › peer-review

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title = "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",

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.",

keywords = "Carbocations, Carbocycles, Cyclization, Enynes, Halogenation, Lewis acids",

author = "Yeh, {Ming Chang P.} and Lin, {Hsin Hui} and Kuo, {Siou Fu} and Chen, {Pei Jie} and Honga, {Jyun Wei}",

note = "Publisher Copyright: {\textcopyright} 2014 Wiley-VCH Verlag GmbH&Co. KGaA, Weinheim.",

year = "2014",

month = dec,

day = "15",

doi = "10.1002/adsc.201400671",

language = "English",

volume = "356",

pages = "3816--3820",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "18",

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T1 - 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

AU - Yeh, Ming Chang P.

AU - Lin, Hsin Hui

AU - Kuo, Siou Fu

AU - Chen, Pei Jie

AU - Honga, Jyun Wei

PY - 2014/12/15

Y1 - 2014/12/15

N2 - 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.

AB - 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.

KW - Carbocations

KW - Carbocycles

KW - Cyclization

KW - Enynes

KW - Halogenation

KW - Lewis acids

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DO - 10.1002/adsc.201400671

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ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 1005789: Experimental Crystal Structure Determination

CCDC 1005787: Experimental Crystal Structure Determination

CCDC 1005788: Experimental Crystal Structure Determination

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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

Abstract

Keywords

ASJC Scopus subject areas

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Datasets

CCDC 1005789: Experimental Crystal Structure Determination

CCDC 1005787: Experimental Crystal Structure Determination

CCDC 1005788: Experimental Crystal Structure Determination

Cite this