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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
Author(s) -
Yeh MingChang P.,
Lin HsinHui,
Kuo SiouFu,
Chen PeiJie,
Hong JyunWei
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400671
Subject(s) - chemistry , aryl , dichloromethane , halo , lewis acids and bases , methylene , medicinal chemistry , ring (chemistry) , stereochemistry , organic chemistry , catalysis , alkyl , physics , quantum mechanics , solvent , galaxy
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 ‐methylene‐bridged bicycles in good yields. This method also provides an easy access to ( E )‐5‐aryl(halo)methylenebicyclo[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.