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Chiral Organometallic Reagents, VII. On the Configurational Stability of α-Methylbenzyllithium

✍ Scribed by Hoffmann, Reinhard W. ;Rühl, Thomas ;Chemla, Fabrice ;Zahneisen, Thomas

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
559 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

α‐Methylbenzyllithium (6) should possess either central or planar chirality. The rate of enantiomerization of 6 at — 78^°^C was found to be faster than its addition to the amide 7, the ketone 8, or to the aldehyde 10, according to a test based on kinetic resolution. The benzyllithium compound 6 thus behaves in THF essentially as a prochiral entity.

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## Abstract Benzyllithium compounds carrying a benzylthio substituent (6), a benzylseleno substituent (8), and an isopropyl(methyl)amino substituent (14) have been generated. Racemization barriers have been determined in THF by monitoring the coalescence of signals of diastereotopic groups in the ^