169783-28-2Relevant academic research and scientific papers
Phosphoric-Carboxylic Anhydrides. New Synthetic Procedures and Reactions with Nucleophiles. Reexamination of the Reaction of Se-alkyl-phosphoroselenoates with Alcohols and Mercuric Trifluoroacetate
Wasiak, J.,Helinski, J.,Dabkowski, W.,Skrzypczynski, Z.,Michalski, J.
, p. 1027 - 1032 (2007/10/02)
Phosphorus trimethylsilyl esters RR'P(O)OSiMe3 react smoothly with carboxylic anhydrides to give phosphoric-carboxylic anhydrides RR'P(O)-O-COR" in excellent yield.A similar reaction proceeds between stannyl esters RR'P(O)OSnMe3 and carboxylic anhydrides.We also have found that the anhydrides RR'P(O)-O-COCF3 are formed in almost quantitative yield when the phosphorus acid halides RR'P(O)X (X=Cl,Br,I) are allowed to react with trifluoroacetic anhydride in the presence of N-methylimidazole. We were able to confirm again that acyclic phosphoric-carboxylic anhydrides exhibit acetylating properties towards amines and alcohols.Our findings contradict with those of Wozniak, Krzyzanowska and Stec relating to the reaction of Se-alkylphosphoroselenoates RR'P(O)SeR" with mercuric trifluoroacetate Hg(OCOCF3)2.Our interpretation of this reaction differs entirely from those presented by the above mentioned authors. Key words: phosphorus-carboxylic anhydrides, Se-alkyl-phosphoroselenoates
