20344-92-7Relevant academic research and scientific papers
Synthesis and Structure of Phenyl-Substituted Bicyclononenes
Quast, Helmut,Knoll, Katja,Peters, Eva-Maria,Peters, Karl,Schnering, Hans Georg von
, p. 777 - 784 (2007/10/02)
Addition of one mole of phenyllithium to bicyclononane-2,6-dione (5) affords the hydroxy ketone 6 besides small amounts of the known diol 7.Dehydration of this mixture by sulfuric acid in acetic acid yields the unsaturated ketone 8 and the diene 1 which are separated by chromatography.Wolff-Kishner reduction of 8 furnished the hydrocarbon 2.In the same way, the known ketones exo- and endo-10 are converted into 4.The preferential formation of the less stable endo-10 is interpreted in terms of the relative stability of the conformations required in the intramolecular aldol reaction of diketone 9.The conformations of 4, 8, exo- and endo-10 are determined by X-ray diffraction analyses.Vicinal proton coupling constants are calculated from torsional anlges and compared to those determined in solutions by high-field NMR spectroscopy.Key Words: Bicyclonon-2-ene, phenyl-substituted derivatives of / Conformation of bicyclonon-2-enes
