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Rotation about the CSe Bond as the Rate‐Determining Step in the Racemization of α‐Selenium‐Substituted Alkyllithium Compounds
Author(s) -
Ruhland Thomas,
Dress Ruprecht,
Hoffmann Reinhard W.
Publication year - 1993
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.199314671
Subject(s) - racemization , selenium , chemistry , rotation (mathematics) , stereochemistry , computational chemistry , medicinal chemistry , organic chemistry , mathematics , geometry
New possibilities for increasing the stability of the configuration of α‐heteroatomsubstituted alkyllithium compounds follow from the unexpected finding that ortho methyl groups influence the rate of racemization of α‐arylselenoalkyllithium compounds. According to this observation, rotation about the CX bond (X Se) [Eq. (a)] can be the rate‐determining step.