| The generation of a cyclopentadienone from a bromocyclopentenone precursor has been studied. The ability of other substituted 2-bromocyclopentenones to generate functionalized cyclopentadienones was examined. The reaction of 2,3-dibromocyclopent-2-enone with amine bases in acetonitrile afforded the bicyclic product shown via generation of a cyclopentadienone and subsequent dimerization.; The reactivity of the bicyclic product with respect to nucleophilic substitution was explored with a number of nucleophiles. Treatment of bicyclic products with sterically unhindered nucleophiles afforded some examples of dimerization products through nucleophilic substitution.; Cyclopentadienone dimers could be converted to indanones for further synthetic study. At high temperature, bicyclic products, which possessed sulfur substituents, were decarbonylated and subsequently aromatized in a non-polar solvent system to produce indanones. |
