Reaction of stereoisomeric bis(cyclohexyl)-2,2′-diones with hydrogen peroxide: structure of the formed adducts

V, N, Khrustalev, Russian Academy of Sciences
Sergey Lindeman, Marquette University
Yu T. Struchkov, Russian Academy of Sciences
E. K. Starostin, Russian Academy of Sciences
A. V. Ignatenko, Russian Academy of Sciences
Gennady I. Nikishin, Russian Academy of Sciences

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.

Abstract

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.