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.
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.
Lu
Yan-Bin
YB
Department of Chemistry, National Tsing Hua University, Hsinchu 30013, Taiwan.
Lee
Tsung-Ho
TH
Liu
Wen-Cheng
WC
Chuang
Gary Jing
GJ
Liao
Chun-Chen
CC
D000475:Alkenes / Q000737:chemistry; D000838:Anions / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009795:Octanes / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D000838:Anions; D001643:Bridged Bicyclo Compounds; D005663:Furans; D009795:Octanes; D014753:Vinyl Compounds; D002244:Carbon; C026728:octane