Generation of acyl anion equivalents from acylphosphonates via phosphonate-phosphate rearrangement: A highly practical method for cross-benzoin reaction

Date

2005-12-09

Author

Demir, Ayhan Sıtkı
Reis, O
Igdir, AC
Esiringu, I
Eymur, S

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Acylphosphonates are potent acyl anion precursors that generate acyl anion equivalents under the promotion of cyanide anion via phosphonate-phosphate rearrangement. These anions readily react with aldehydes to provide cross-benzoin products. In this way it is possible to synthesize a variety of aromatic-aromatic, aromatic-aliphatic, and aliphatic-aromatic benzoins. Moreover the reaction of benzoylphosphonate with potent electrophile 2,2,2-trifluoroacetophenone provided the corresponding aldehyde-ketone coupling product in high yield.

Subject Keywords

Organic Chemistry

URI

https://hdl.handle.net/11511/56737

Journal

JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1021/jo051811u

Collections

Department of Chemistry, Article

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Citation Formats

A. S. Demir, O. Reis, A. Igdir, I. Esiringu, and S. Eymur, “Generation of acyl anion equivalents from acylphosphonates via phosphonate-phosphate rearrangement: A highly practical method for cross-benzoin reaction,” JOURNAL OF ORGANIC CHEMISTRY, pp. 10584–10587, 2005, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56737.