Protonation of acyl anion equivalents generated from acylphosphonates: nonhydride access to the aldehyde oxidation state from the carboxylic acid oxidation state |
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Authors: | Ayhan S Demir Ömer Reis Ilker Esiringü Barbaros Reis Sehriban Baris |
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Institution: | Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey |
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Abstract: | Acylphosphonates, which are easily available from carboxylic acids, are potent acyl anion precursors and undergo cyanide ion promoted phosphonate-phosphate rearrangement to provide the corresponding acyl anion equivalents as reactive intermediates. The protonation of these acyl anion equivalents furnished cyanohydrin O-phosphates in good yields. For the high yield formation of cyanohydrin O-phosphates from arylphosphonates THF should be used and from alkylphosphonates DME was used. |
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Keywords: | Acylphosphonates Cyanohydrin O-phosphates Acyl anion Rearrangements Carboxylic acids |
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