Reaction of stereoisomeric bis(cyclohexyl)-2,2′-diones with hydrogen peroxide: structure of the formed adducts
Russian Chemical Bulletin
The reaction of meso- and D,L-forms of bis(cyclohexyl)-2,2′-dione with a methanol solution of hydrogen peroxide in a neutral medium has been studied. It has been established that in the case of the D,L-formrac-(1R,4R,9S,10S)-1,4-dihydroxy-2,3-dioxatricyclo-[8.4.0.04,9] tetradecane is formed, while the meso-form affords rac-(1R,4R,9S,10R)-1-methoxy-4-hydroxy-2, 3-dioxatricyclo[8.4.0.04,9]tetradecane. The structures of the compounds have been established by X-ray structural analysis and by 1H and 13C NMR spectroscopy.
Khrustalev, V. N.; Lindeman, Sergey V.; Struchkov, Yu T.; Starostin, E. K.; Ignatenko, A. V.; and Nikishin, Gennady I., "Reaction of stereoisomeric bis(cyclohexyl)-2,2′-diones with hydrogen peroxide: structure of the formed adducts" (1995). Chemistry Faculty Research and Publications. 643.