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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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

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Citation Formats

A. S. Demir, O. Reis, I. Esiringu, B. Reis, and S. Baris, “Protonation of acyl anion equivalents generated from acylphosphonates: nonhydride access to the aldehyde oxidation state from the carboxylic acid oxidation state,” TETRAHEDRON, pp. 160–165, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57572.