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5,5-dimethylcyclononanone absorption acetic acid acetone acid phthalate activation energy acyloin acyloin acetate added alcohol amine Anal anhydrous aqueous layer asymmetric benzene Calc'd carbonyl catalyst CHaCHaBr CHCl cinchonidine colorless condensation conformation COOEt cooled copper powder crop crude crystallisation crystals cyclization cyclononanone decomposed decomposition derivative diazonium salt diazotized diethyl diluted dissolved distilled ester ethanol evaporated extracted with ether filtration flask fluoborate formation Fraction gave hexane hydrochloric acid hydrogen indazole infrared isomer ketone lithium aluminum hydride manometer medium size ring melting point mixture was heated mole mother liquors nine membered ring nitrogen olefin optically active oxidation phenanthrene potassium procedure pure quantitative quinine salt quinoxaline racemization reaction mixture recrystallized refluxing regenerated residue resolution resolving agent ring compounds room temperature rotation salt was obtained saturated showed sodium carbonate sodium hydroxide solid solution solvent spectra stirring sulfuric acid synthesis trans xylene yellow yield of phenanthrene