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Issue 73, 2014
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A lithiomethyl trimethylammonium reagent as a methylene donor

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Abstract

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.

Graphical abstract: A lithiomethyl trimethylammonium reagent as a methylene donor

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Publication details

The article was received on 16 Jun 2014, accepted on 17 Jul 2014 and first published on 30 Jul 2014


Article type: Communication
DOI: 10.1039/C4CC04579C
Author version available: Download Author version (PDF)
Citation: Chem. Commun., 2014,50, 10604-10607
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    A lithiomethyl trimethylammonium reagent as a methylene donor

    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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