Methyl propiolate explained

Methyl propiolate is an organic compound with the formula HC2CO2CH3. It is the methyl ester of propiolic acid, the simplest acetylenic carboxylic acid. It is a colorless liquid that is miscible with organic solvents. The compound is a reagent and building block for the synthesis of other organic compounds, reactions that exploit the electrophilicity of the alkyne group.[1] For example it is a potent dienophile.[2] It has been widely evaluated as a precursor to heterocycles.[3] including 1,3-dipolar cycloadditions.[4]

References

  1. Encyclopedia: Gavin C.. Hirst. 2001. 10.1002/047084289X.rm237. Encyclopedia of Reagents for Organic Synthesis. Methyl Propiolate. 0471936235.
  2. 10.1016/s0040-4020(02)00410-6 . Quantitative characterization of the global electrophilicity power of common diene/Dienophile pairs in Diels–Alder reactions . 2002 . Domingo . Luis R. . Aurell . M.José . Pérez . Patricia . Contreras . Renato . Tetrahedron . 58 . 22 . 4417–4423 .
  3. 10.1021/ja201143v . Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies . 2011 . Guimond . Nicolas . Gorelsky . Serge I. . Fagnou . Keith . Journal of the American Chemical Society . 133 . 16 . 6449–6457 . 21452842 .
  4. 10.1021/ol060283l . Reusable Polymer-Supported Catalyst for the [3+2] Huisgen Cycloaddition in Automation Protocols . 2006 . Girard . Christian . Önen . Esra . Aufort . Marie . Beauvière . Sophie . Samson . Edmond . Herscovici . Jean . Organic Letters . 8 . 8 . 1689–1692 . 16597142 .

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