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Relative Migratory Aptitude of Substituents and Stereochemistry of Dyotropic Ring Enlargements of β‐Lactones
Author(s) -
Mulzer Johann,
Hoyer Karsten,
MüllerFahrnow Anke
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199714761
Subject(s) - ring (chemistry) , aptitude , stereochemistry , chemistry , medicinal chemistry , organic chemistry , psychology , developmental psychology
Not concerted, but stepwise: Dyotropic ring enlargement of β‐lactones 1 to γ‐lactones 2 proceeds via the zwitterionic intermediate Z‐1 (σ‐and π‐donor substituents). The relative migratory aptitude of the substituents is π‐donor > n‐donor > σ‐donor.
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