Reaction of stereoisomeric bis(cyclohexyl)-2,2′-diones with hydrogen peroxide: structure of the formed adducts
Russian Chemical Bulletin, Vol. 44, No. 5 (May 1995): 907-912. DOI.
Sergey Lindeman was affiliated with A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russian Federation at the time of publication.
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.