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


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

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

  • 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.