ArticleMolecules (Basel, Switzerland)2021
Selective Esterification of Phosphonic Acids.
Article in Molecules (Basel, Switzerland), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed.
- Dealkylation as a Strategy to Synthesize Unconventional Lithium Salts fromInorganic chemistry · 2026Article
- Synthesis of Novel 1,3,4-Oxadiazole-DerivedPharmaceutics · 2022Article
- The Synthesis and Evaluation of Diethyl Benzylphosphonates as Potential Antimicrobial Agents.Molecules (Basel, Switzerland) · 2022Article
- Promiscuous Lipase-Catalyzed Markovnikov Addition of H-Phosphites to Vinyl Esters for the Synthesis of Cytotoxic α-Acyloxy Phosphonate Derivatives.Materials (Basel, Switzerland) · 2022Article
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4 authors.
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Abstract
Here, we report straightforward and selective synthetic procedures for mono- and diesterification of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono- or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The substrate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small- and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30 °C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters.
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