A lithiomethyl trimethylammonium reagent as a methylene donor

Straightforward deprotonation of soluble tetramethylammonium salts with alkyllithium reagents gives lithiomethyl trimethylammonium reagents. Coordination of the Li cation is crucial to the stability of these 'N-C ylides'. These reagents were used to prepare epoxides, aziridines and allylic...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2014-01, Vol.50 (73), p.10604-10607
Main Authors: den Hartog, Tim, Sarria Toro, Juan M, Couzijn, Erik P A, Chen, Peter
Format: Article
Language:English
Subjects:
Alcohols
Cations
Methylene
Reagents
Stability
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Summary:Straightforward deprotonation of soluble tetramethylammonium salts with alkyllithium reagents gives lithiomethyl trimethylammonium reagents. Coordination of the Li cation is crucial to the stability of these 'N-C ylides'. These reagents were used to prepare epoxides, aziridines and allylic alcohols.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc04579c