Simplifying metal-‘ate’ chemistry: formation and comprehensive characterisation of a homo-metallic amido lithiate complex

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)(CH₂CHCH₂)}₂]. ⁷Li NMR and computational calculations indicate this model to be representative of the solution state, with ¹H and ¹³C NMR showing a 1,3-sigmatropic rearrangement. [Li{N(1-naph)(CH₂CHCH₂)}·Et₂O]₂1, and [Li{N(1-naph) (CH₂CHCH₂)}·PMDETA] 3, are presented for comparison.