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Die Herstellung von 3, 5‐disubstituierten Cyclopentenen durch Ozonolyse von Norbornadien
Author(s) -
Grob C. A.,
Pfaendler H. R.
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530828
Subject(s) - chemistry , sodium borohydride , norbornadiene , cyclopentene , catalytic hydrogenation , medicinal chemistry , catalysis , sodium carbonate , organic chemistry , polymer chemistry , sodium
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 LiAlH 4 . 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.