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Synthesis of 1‐Bicyclo [3.2.2]nonene and 1 (7)‐Bicyclo [3.2.2]nonene by Intramolecular Wittig Reaction
Author(s) -
Becker Konrad B.,
Chappuis Jacques L.
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630709
Subject(s) - bicyclic molecule , chemistry , intramolecular force , wittig reaction , furan , cyclobutane , ring (chemistry) , stereochemistry , dimer , organic chemistry
The synthesis of 1‐bicyclo[3.2.2]nonene (2) and of 1 (7)‐bicyclo [3.2.2]nonene (3) , two isomeric bridged ( E )‐cycloheptenes, by intramolecular Wittig reaction is described. These ‘ Bredt olefins’ could not be isolated, but dimerized rapidly. In both cases, the main product was shown to be a head‐to‐tail dimer with a cyclobutane ring. The ‘ Bredt olefins’ were also trapped in situ with furan or 2,5‐diphenylbenzo [ c ]furan.
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