The formation of hemiacetals from aldehydes and alcohols is quite well known, as these are usually developed as intermediates in the preparation of acetals from aldehydes or ketones. Nevertheless, as far as we know, the examples of transformation of imines into hemiacetals are very scarce, and this reaction seems to be promoted by coordination to a metal ion. In this work, we describe the partial hydrolysis of a Schiff base, and its subsequent evolution to an hemiacetal donor in the presence of dysprosium(III) in an alcoholic medium. Full characterization of the final product, including single X-ray studies, is reported.
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Hemiacetal formation from a Schiff base in the presence of dysprosium(III)
Published: 14 November 2019 by MDPI in The 23rd International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Keywords: hemiacetal, imine hydrolysis, dysprosium(III)