Mn-trimethyltriazacyclononane/ascorbic acid: A remarkably efficient catalyst for the epoxidation of olefins and the oxidation of alcohols with hydrogen peroxide

Article abstract of DOI:10.1016/S0040-4039(99)01595-6

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.