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.
ASJC Scopus subject areas
- Organic Chemistry