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Updated: Mar 19, 2026

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
Simplifying metal-'ate' chemistry: formation and comprehensive characterisation of a homo-metallic amido lithiate
Jamie A Greer1, Victoria L Blair1, Christopher D Thompson1
1School of Chemistry, Monash University, Clayton, Victoria 3168, Australia. phil.andrews@monash.edu.
Abstract:
Addition of TMEDA to lithium allyl-1-naphthylamide in a 1 : 1 ratio afforded the novel amido lithium/lithiate complex, [Li(TMEDA)2][Li{N(1-naph)(CH2CH[double bond, length as m-dash]CH2)}2]. (7)Li NMR and computational calculations indicate this model to be representative of the solution state, with (1)H and (13)C NMR showing a 1,3-sigmatropic rearrangement. [Li{N(1-naph)(CH2CH[double bond, length as m-dash]CH2)}·Et2O]2, and [Li{N(1-naph) (CH2CH[double bond, length as m-dash]CH2)}·PMDETA] , are presented for comparison.
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