Premium
A Note on Stereochemical Observations of the Deprotonation of Ethyl 2‐Alkenoates
Author(s) -
Krebs ErnstPeter
Publication year - 1981
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.19810640407
Subject(s) - chemistry , deprotonation , protonation , stereochemistry , medicinal chemistry , organic chemistry , ion
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.