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

Authors

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

Document Type

Article

Language

eng

Publication Date

5-1995

Publisher

Springer

Source Publication

Russian Chemical Bulletin

Source ISSN

1066-5285

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-[8.4.0.0^4,9] tetradecane is formed, while the meso-form affords rac-(1R,4R,9S,10R)-1-methoxy-4-hydroxy-2, 3-dioxatricyclo[8.4.0.0^4,9]tetradecane. The structures of the compounds have been established by X-ray structural analysis and by ¹H and ¹³C NMR spectroscopy.

Comments

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.

Recommended Citation

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.
https://epublications.marquette.edu/chem_fac/643