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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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Ernst‐Peter Krebs (1981) studied this question.
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