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A Note on Stereochemical Observations of the Deprotonation of Ethyl 2-Alkenoates

✍ Scribed by Ernst-Peter Krebs

Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
167 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Deprotonation of ethyl (E)‐2‐alkenoates 1, 3 and 4 yields after protonation the double bond migrated (3 Z)‐isomers 5, 7 and 9 as major products. In contrast, deprotonation and reprotonation of ethyl (Z)‐2‐pentenoate (2) gives the (3 E)‐isomer 6 exclusively. These findings are explained by reaction paths starting from different ester conformations.

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