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- W2054051955 abstract "Die Ozonide 5, 11 und 18 reagieren wie die als Zwischenprodukte auftretenden 1,4-Diketone mit Lithiumaluminiumhydrid zu Gemischen von d, l- und meso-Diolen. Die an den NMR-Signalen für die diastereotopen Methylgruppen ablesbaren Stereoselektivitäten für d, l- und meso-Formen werden mit einer intramolekularen Diastereoface-Differenzierung auf der Stufe der Ketoalkohole und der intermediären Ausbildung von Komplexen des Typs 36 (cyclisches Modell) gedeutet. Die stereochemischen Analyse wird durch die ohne Konfigurationsänderung ablaufende Über-führung der Diole in die entsprechenden cis, trans-isomeren Ketale bzw. Acetale bestätigt. Wasserabspaltung aus den zweiwertigen Alkoholen führt nach Art einer nucleophilen inneren Substitution stereospezifisch zu cis, trans-isomeren cyclischen Ethern. Concerning the Stereoselectivity of the Reduction of Ozonides and 1,4-Diketones with Lithium Aluminium Hydride (1,4-Induction) The ozonides 5, 11, and 18 as well as the intermediate 1,4-diketones react with lithium aluminium hydride to give mixtures of d, l- and meso-diols. The stereoselectivity for d, l- and meso-forms evaluated by integration of the NMR signals of the diastereotopic methyl groups can be explained by intramolecular diastereoface differentiation at the stage of the keto alcohols and with the intermediate formation of complexes of type 36 (cyclic model). The stereochemical analysis is confirmed by transformation of the diols into the corresponding cis, trans-ketals or acetals which occurs without configurational changes. Elimination of water from the diols leads stereospecifically to cyclic cis, trans-isomeric ethers via an intramolecular nucleophilic substitution." @default.
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- W2054051955 date "1978-10-01" @default.
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- W2054051955 title "Über die Stereoselektivität der Reduktion von Ozoniden und 1,4-Diketonen mit Lithiumaluminiumhydrid (1,4-Induktion)" @default.
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- W2054051955 doi "https://doi.org/10.1002/cber.19781111015" @default.
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