In situ Formation of Peracetic Acid in Iron-Catalyzed Epoxidations by Hydrogen Peroxide in the Presence of Acetic Acid

✍ Scribed by Megumi Fujita; Lawrence Que Jr.

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 102 KB
• Volume: 346
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200303204

✦ Synopsis

Abstract

Iron complexes (tpa)Fe(OTf)~2~ (1) and (bpmen)Fe(OTf)~2~ (2) [tpa=tris‐(2‐pyridylmethyl)amine; bpmen=N,N′‐bis‐(2‐pyridylmethyl)‐__N,N′‐__dimethyl‐1,2‐ethylenediamine] were found to catalyze the in situ formation of AcOOH from H~2~O~2~ and AcOH in the course of olefin oxidations. While oxidation of cyclooctene by H~2~O~2~ catalyzed by 1 gives nearly equimolar epoxide and cis‐diol products, introduction of AcOH to the reaction greatly enhances the selectivity for epoxidation. The resulting product distribution is nearly identical to that of cyclooctene oxidation by AcOOH catalyzed by 1. The in situ generation of AcOOH from H~2~O~2~ and AcOH in epoxidation catalyzed by some iron complexes opens a possibility to attain AcOOH‐type efficiency of epoxidation using H~2~O~2~ as a terminal oxidant.