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- W1551400534 abstract "Die Reduktion von 1-Methyl-4-tosyloxy-bicyclo [2.2.2] octanon-(2) (2) mit Lithiumalanat führt, unabhängig vom Lösungsmittel, unter Fragmentierung zum 1-Methyl-1-hydroxymethyl-4-methylen-cyclohexan (4). Im Gegensatz dazu ist der Verlauf der Reduktion des 1-Methyl-4-tosyloxy-bicyclo[2.2.2]octanon-(2)-äthylenacetals (12) stark vom Lösungsmittel abhängig. In heterogenerÄtherphase erfolgt Fragmentierung, in homogener Tetrahydrofuranlösung O-;S-Spaltung unter Rückbildung des zugrundeliegenden Alkohols11. Dieser Reaktionsverlauf wird auf die unterschiedliche Solvation des Reduktionsmittels zurückgeführt. The reduction of 1-methyl-4-tosyloxy-bicyclo[2.2.2]octan-2-one (2) with LAH proceeds by fragmentation to 1-methyl-4-hydroxymethyl-4-methylene-cyclohexane (4) without any influence of the solvent on the product composition. On the other hand the course for the reduction of 1-methy-4-tosyloxy-bicyclol 2.2.2|octanon-2-ethylene acetal (12) depends on the nature of the solvent. Suspensions of LAH in diethyl ether give fragmentation reactions, homogeneous solutions in tetrahydrofurane lead to a cleavage of the OS bond with the result that the original alcohol11 is reformed. The results are referred to solvation effects on the reducing agent." @default.
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- W1551400534 date "1969-01-01" @default.
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- W1551400534 title "Reduktive fragmentierung—III" @default.
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- W1551400534 doi "https://doi.org/10.1016/s0040-4020(01)82901-x" @default.
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