Oxime ether (R2C=NOR) functionality is formed through the condensation of alkoxyamine (RONH2) and carbonyl (e.g., aldehyde/ketone) substrates.  It is present in various natural products and pharmaceuticals (e.g., antibiotics).  The stability and ease of formation of the oxime ether bond render it useful for various applications.  As part of our collaborative study on surfactant properties that affect the surface tension of water, we utilized the oxime ether bond to vary the surfactant properties.  The key step in our surfactant synthesis is the condensation of an alkoxyamine (carrying a hydrophobic alkyl chain) and a carbonyl substrate (carrying a hydrophilic sugar group).  Our synthesis allows for the facile variation of both the hydrophobic and hydrophilic portions of the oxime ether surfactant. The details of our synthetic approach will be presented.  Surface tension studies utilizing our oxime ether surfactants will be presented elsewhere.

Oxime ether surfactants: Versatile surface tension modifiers

243rd National Meeting (2012)

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