The treatment of dimethyl malonate with LHMDS in anhydrous THF (condensed-phase) generates, in addition to the expected corresponding lithium enolate, methyl formate anion (or methoxycarbonyl anion, -COOMe) which can react with several electrophiles to give corresponding methoxycarbonyl derivatives by nucleophilic substitution reaction.
Dimethyl malonate/LHMDS system as a new protocol for generating methyl formate anion (-COOMe) in the condensed-phase / V. Di Bussolo, S. Princiotto, E. Martinelli, V. Bordoni, P. Crotti. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 57:15(2016 Apr 13), pp. 1644-1647. [10.1016/j.tetlet.2016.02.090]
Dimethyl malonate/LHMDS system as a new protocol for generating methyl formate anion (-COOMe) in the condensed-phase
S. PrinciottoSecondo
;
2016
Abstract
The treatment of dimethyl malonate with LHMDS in anhydrous THF (condensed-phase) generates, in addition to the expected corresponding lithium enolate, methyl formate anion (or methoxycarbonyl anion, -COOMe) which can react with several electrophiles to give corresponding methoxycarbonyl derivatives by nucleophilic substitution reaction.
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