One-pot formation of 2,4-di- or 2,4,6-tri-olefinic monocarboxylic acids by straight chain C4-extension

We report a one-pot formation of 2,4-diolefinic or 2,4,6-triolefinic monocarboxylic acids, R-(CH[bond, double bond]CH)(2or3)-COOH, by decarboxylative condensation of an optionally α,β-unsaturated aldehyde with glutaconic acid, HOOC-CH(2)-CH[bond, double bond]CH-COOH as straight chain C4-extender. Th...

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Detalles Bibliográficos
Autores principales: Sobotta, Jessica, Schmalhofer, Maximilian, Steiner, Thomas M., Eisenreich, Wolfgang, Wächtershäuser, Günter, Huber, Claudia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5537201/
https://www.ncbi.nlm.nih.gov/pubmed/28795165
http://dx.doi.org/10.1016/j.heliyon.2017.e00368
Descripción
Sumario:We report a one-pot formation of 2,4-diolefinic or 2,4,6-triolefinic monocarboxylic acids, R-(CH[bond, double bond]CH)(2or3)-COOH, by decarboxylative condensation of an optionally α,β-unsaturated aldehyde with glutaconic acid, HOOC-CH(2)-CH[bond, double bond]CH-COOH as straight chain C4-extender. The reaction is broadly applicable to saturated and unsaturated aldehydes and opens up a simple gateway to valuable organic products and reactive intermediates.

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