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1,3‐ and 1,2‐Carbo‐Migration of 2‐Vinylbicyclo[2.2.2]octenols: Facile and Concise Synthesis of Bicyclo[4.2.2]/[3.2.2] Skeleton by Two/One‐Carbon Ring Expansion
Author(s) -
Lu YanBin,
Lee TsungHo,
Liu WenCheng,
Chuang Gary Jing,
Liao ChunChen
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200800113
Subject(s) - bicyclic molecule , ring (chemistry) , olefin fiber , stereochemistry , chemistry , carbon skeleton , organic chemistry , catalysis
Abstract The synthesis of a series of bicyclo[4.2.2]octenones and bicyclo[3.2.2]heptenones by 1,3‐ or 1,2‐migration reaction from 2‐vinylbicyclo[2.2.2]octenols is reported. These ring‐expansion reactions were accomplished under basic or neutral conditions. Whether 1,3‐ or 1,2‐migration takes place depends on endo‐ or exocyclic olefin displacement in the substrates.