Insight into the Behaviour of a Lithium Enolate in Solution   tert-Butyloxodioxolaneacetic acid was dilithiated to the enolate with LDA, then treated with MeCO2D, and finally with CH2N2 to give the deuterated ester. Two different stable forms of the enolate were produced, depending on whether the deprotonation of was carried out in toluene or in THF. The generated (Me2CH)2NH was coordinated to the enolate and, hence, served as a strong lipophilic solvating agent. LDA could substitute the amine ligands of the two species to a different extent. THF was partially able to displace (Me2CH)2NH in toluene, but the coordination of the amine to the enolate produced in THF was quantitative.