Tetrahedron Letters p. 7965 - 7968 (1999)
Update date:2022-08-16
Topics:
Berkessel, Albrecht
Sklorz, Christoph A.
The system comprised of manganese(II) acetate or sulfate, 1,4,7-trimethyl-1,4,7-triazacyclononane (TMTACN) and ascorbic acid efficiently catalyzes the epoxidation of olefins and the oxidation of alcohols with hydrogen peroxide. For example, in the presence of as little as 0.03 mol% of Mn2+, methyl acrylate is converted to its epoxide in 97% yield. Under the same conditions, 2-pentanol yielded 2-pentanone in almost quantitative yield. With E- and Z-1-deuterio-1-octene as substrates, the epoxidation was shown to proceed with almost exclusive (94±2%) retention of configuration.
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