On the Palladium-catalyzed Hydrogenolysis of the Epoxysuccinic Acids1

Oscar Gawron, Thomas P. Fondy, Donald J. Parker

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The hydrogenolysis of cis-epoxysuccinic acid and trans-epoxysuccinic acid in aqueous solution with palladium-on-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
DOIs
StatePublished - Mar 1 1963
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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