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

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

10 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	3816-3820
頁數	5
期刊	Advanced Synthesis and Catalysis
卷	356
發行號	18
DOIs	https://doi.org/10.1002/adsc.201400671
出版狀態	已發佈 - 2014 12月 15

ASJC Scopus subject areas

催化
有機化學

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10.1002/adsc.201400671

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Link to publication in Scopus

CCDC 1005786: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Lin, H. (Creator), Kuo, S. (Creator), Chen, P. (Creator) & Honga, J. (Contributor), Unknown Publisher, 2015
DOI: 10.5517/cc12rlq4, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc12rlq4&sid=DataCite
資料集: Dataset
CCDC 1005787: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Lin, H. (Creator), Kuo, S. (Creator), Chen, P. (Creator) & Honga, J. (Contributor), Unknown Publisher, 2015
DOI: 10.5517/cc12rlr5, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc12rlr5&sid=DataCite
資料集: Dataset
CCDC 1005788: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Lin, H. (Creator), Kuo, S. (Creator), Chen, P. (Creator) & Honga, J. (Contributor), Unknown Publisher, 2015
DOI: 10.5517/cc12rls6, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc12rls6&sid=DataCite
資料集: Dataset

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@article{882ebbc4f5234e81808d7fd4b54c9c85,

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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TY - JOUR

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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U2 - 10.1002/adsc.201400671

DO - 10.1002/adsc.201400671

M3 - Article

AN - SCOPUS:84915747156

SN - 1615-4150

VL - 356

SP - 3816

EP - 3820

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 18

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

摘要

ASJC Scopus subject areas

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其它文件與鏈接

指紋

資料集

CCDC 1005786: Experimental Crystal Structure Determination

CCDC 1005787: Experimental Crystal Structure Determination

CCDC 1005788: Experimental Crystal Structure Determination

引用此