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

ABSTRACT: We report a one-pot formation of 2,4-diolefinic or 2,4,6-triolefinic monocarboxylic acids, R-(CH 000000000000 000000000000 000000000000 111111111111 000000000000 111111111111 000000000000 000000000000 000000000000 CH)_2or3-COOH, by decarboxylative condensation of an optionally ?,?-unsaturated aldehyde with glutaconic acid, HOOC-CH₂-CHCH-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.

SUBMITTER: Sobotta J

PROVIDER: S-EPMC5537201 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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

Sobotta Jessica J Schmalhofer Maximilian M Steiner Thomas M TM Eisenreich Wolfgang W Wächtershäuser Günter G Huber Claudia C

Heliyon 20170727 7

We report a one-pot formation of 2,4-diolefinic or 2,4,6-triolefinic monocarboxylic acids, R-(CH[bond, double bond]CH)<sub>2or3</sub>-COOH, by decarboxylative condensation of an optionally α,β-unsaturated aldehyde with glutaconic acid, HOOC-CH<sub>2</sub>-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. ...[more]

PMID: 28795165

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