On the palladium-catalyzed hydrogenolysis of the epoxysuccinic acids

Oscar Gawron, Thomas P Fondy, Donald J. Parker

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Abstract

The hydrogenolysis of cis-epoxysuccinic acid and trans-epoxysuccinic acid in aqueous solution with palladiumon-charcoal catalyst leads to the formation of malic acid, succinic acid, and diglycolic acid. Hydrogenolysis of the epoxides to malic acid proceeds in a trans fashion, threo-3-deuterio-DL-malic acid and erythro-3-deuterio-DL-malic acid resulting from cis-epoxysuccinic acid and trans-epoxysuccinic acid, respectively. Mixed erythro- and threo-2,3-dideuteriosuccinic acids result from cis-epoxysuccinic acid and threo-2,3-dideuteriosuccinic acid results from trans-epoxysuccinic acid. Malic acid is not an intermediate for the formation of succinic acid.

Original languageEnglish (US)
Pages (from-to)700-703
Number of pages4
JournalJournal of Organic Chemistry
Volume28
Issue number3
StatePublished - 1963
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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