Die Herstellung von 3, 5-disubstituierten Cyclopentenen durch Ozonolyse von Norbornadien |
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Authors: | C. A. Grob H. R. Pfaendler |
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Abstract: | The ozonization of norbornadiene is described. Oxidation of the intermediate with silver oxide furnishes 4-cyclopentene-cis-1, 3-dicarboxylic acid, reduction with sodium borohydride cis-1, 3-bis-hydroxymethylcyclopent-4-ene. The latter was converted to cis-3, 5-dimethylcyclopentene by reduction of the corresponding bis-tosylate with LiAlH4. Hydrogenation of the ozonization intermediate over palladium-lead carbonate (Lindlar's catalyst) afforded 4-cyclopentene-cis-1, 3-dialdehyde. This reaction represents a new and selective method for the reduction of unsaturated ozonization intermediates. |
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