Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies on Geometric Isomerism by Nuclear Magnetic Resonance. II. Geometric Configurations of Alkylidenecyanoacetic Esters
Toshio HayashiMinoru IgarashiShoichi HayashiHiroshi Midorikawa
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1965 Volume 38 Issue 12 Pages 2063-2067


The Knoevenagel reaction of a methyl alkyl ketone with cyanoacetic ester gives a stereoisomeric mixture of α-cyano-β-alkylcrotonic ester. The NMR technique has been applied to the study of the geometric configurations of the mixture. It has been found that the isomer with a β-methyl group cis to the alkoxycarbonyl group always occurs predominantly. The magnitude of the cis-trans composition of the mixture is parallel to the steric requirement of the β-substituted alkyl group.

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