On the palladium-catalyzed hydrogenolysis of the epoxysuccinic acids

Oscar Gawron, Thomas P Fondy, Donald J. Parker

Research output: Contribution to journalArticle

6 Citations (Scopus)

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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Hydrogenolysis
Palladium
Acids
NSC 153174
Succinic Acid
Charcoal
Epoxy Compounds
malic acid
Catalysts

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

On the palladium-catalyzed hydrogenolysis of the epoxysuccinic acids. / Gawron, Oscar; Fondy, Thomas P; Parker, Donald J.

In: Journal of Organic Chemistry, Vol. 28, No. 3, 1963, p. 700-703.

Research output: Contribution to journalArticle

Gawron, Oscar ; Fondy, Thomas P ; Parker, Donald J. / On the palladium-catalyzed hydrogenolysis of the epoxysuccinic acids. In: Journal of Organic Chemistry. 1963 ; Vol. 28, No. 3. pp. 700-703.
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