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Synfacts 2010(10): 1199-1199  
DOI: 10.1055/s-0030-1258661
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Flow Ozonolysis Using a Semipermeable Teflon AF-2400 Membrane

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Maki Minakawa
M. O’Brien, I. R. Baxendale, S. V. Ley*
University of Cambridge, UK
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Publication History

Publication Date:
22 September 2010 (online)

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Significance

A simple and convenient flow chemistry device to bring about the ozonolysis of exomethylenes via gas-to-liquid transfer through semipermeable Teflon AF-2400 tubing was ­developed. Using a Teflon AF-2400 tubing (90 cm length) connected to a syringe pump (Infors AG, HT-Precidor), the flow ozonolysis of a series of ­exomethylenes was carried out in methanol with one hour of residence time to give the corresponding ketones (10 examples, 73-95% yield). A citronellol derivative (C10-OTBS) was converted into a C7-OTBS aldehyde under similar conditions in 57% yield.