Molecular and crystal structure of ethylene acetal of <Emphasis Type="Italic">endo</Emphasis>-<Emphasis Type="Italic">endo</Emphasis>-3-trityloxymethylbicyclo[3.3.1]nonane-2-on-7-ol |
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| Authors: | O N Zefirova L A Zasurskaya E V Nurieva N V Zyk N S Zefirov |
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| Institution: | (1) Chemistry Department of M.V.Lomonosov Moscow State University, Moscow, 119992, Russia;(2) Institute of Physiologically Active Compounds of Russian Academy of Science, 142432, Chernogolovka, Noginsky district, Moscow region, Russia |
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| Abstract: | Molecular structure of ethylene acetal of 3-trityloxymethylbicyclo3.3.1]nonane-2-on-7-ol (3) was determined by X-ray investigation. It was revealed that 3 has endo-endo-configuration and adopt chair-boat-conformation. The distortion of rings was evaluated by calculation of the Zefirov–Palyulin and Cremer–Pople puckering parameters.
Failure of esterification of 3 was rationalized in terms of steric hindrance and intramolecular hydrogen bonding.
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| Keywords: | Substituted bicyclo[3 3 1]nonane Steric hindrance Trityl group X-ray study Conformation Hydrogen bond |
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