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Reductive carboxylation of aromatic esters by electron transfer from magnesium metal.
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Jan2017, Vol. 58 Issue 3, p206-209. 4p. - Publication Year :
- 2017
-
Abstract
- Magnesium-promoted reductive carboxylation of ethyl benzoate in the presence of chlorotrimethylsilane in N , N -dimethylformamide brought about a new carbon-carbon bond formation between the carbonyl carbon atom and carbon dioxide to give the corresponding benzoylformic acid in good yield. It is noteworthy that only ethyl benzoates with substituents at the meta -position were converted into benzoylformic acid derivatives. Moreover, no mandelic acid was detected even under the reductive conditions. This result indicates that benzoylformic acid was obtained after hydrolysis of a carboxylated intermediate, which would be alive as a stabilized structure in the reaction media. [ABSTRACT FROM AUTHOR]
- Subjects :
- *CARBOXYLATION
*CHEMICAL reduction
*ESTERS
*CHARGE exchange
*MAGNESIUM
*METHYLSILANE
Subjects
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 58
- Issue :
- 3
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 120403112
- Full Text :
- https://doi.org/10.1016/j.tetlet.2016.12.001