Issue 73, 2014

A lithiomethyl trimethylammonium reagent as a methylene donor

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

Supplementary files

Article information

Article type
Communication
Submitted
16 Jun 2014
Accepted
17 Jul 2014
First published
30 Jul 2014

Chem. Commun., 2014,50, 10604-10607

Author version available

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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