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Protonation of acyl anion equivalents generated from acylphosphonates: nonhydride access to the aldehyde oxidation state from the carboxylic acid oxidation state
Date
2007-01-01
Author
Demir, Ayhan Sıtkı
Reis, Omer
Esiringu, Ilker
Reis, Barbaros
Baris, Sehriban
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Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
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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.
Subject Keywords
Organic Chemistry
,
Biochemistry
,
Drug Discovery
URI
https://hdl.handle.net/11511/57572
Journal
TETRAHEDRON
DOI
https://doi.org/10.1016/j.tet.2006.10.036
Collections
Department of Chemistry, Article