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.
T. den Hartog, J. M. Sarria Toro, E. P. A. Couzijn and P. Chen, Chem. Commun., 2014, 50, 10604 DOI: 10.1039/C4CC04579C
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