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

✍ Scribed by Albrecht Berkessel; Christoph A. Sklorz

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 253 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)01595-6

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✦ Synopsis

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 Mn 2÷, 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-l-deuterio-l-octene as substrates, the epoxidation was shown to proceed with almost exclusive (94+2%) retention of configuration.

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