Cyanide Ion Promoted Addition of Acylphosphonates to Diethyl Cyanophosphonate: Synthesis of Phosphonocyanohydrin O-Phosphates

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DEMİR A. G. , Aybey A., Emrullahoglu M.

SYNTHESIS-STUTTGART, no.10, pp.1655-1658, 2009 (SCI-Expanded)

• Publication Type: Article / Article
• Publication Date: 2009
• Doi Number: 10.1055/s-0029-1216634
• Journal Name: SYNTHESIS-STUTTGART
• Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
• Page Numbers: pp.1655-1658
• Keywords: phosphonocyanohydrins, diethyl cyanophosphonate, addition reactions, acyl phosphonates, nucleophilic additions, ACYL ANION EQUIVALENTS, CARBONYL-COMPOUNDS, BINOLAM-ALCL, PHOSPHORYLATION, REARRANGEMENT, PHOSPHONATES, CONVERSION, NITRILES, CATALYST, COMPLEX
• Middle East Technical University Affiliated: Yes

Abstract

Cyanide ion catalyzed addition of acylphosphonates to diethyl cyanophosphonate furnished phosphonocyanohydrin O-phosphates in high yield. The reaction works via the phosphonate-phosphate rearrangement, followed by the addition of diethyl cyanophosphonate to the cyanohydrin phosphate anion.