PHOSPHORIC-CARBOXYLIC ANHYDRIDES - NEW SYNTHETIC PROCEDURES AND REACTIONS WITH NUCLEOPHILES - REEXAMINATION OF THE REACTION OF SE-ALKYL-PHOSPHOROSELENOATES WITH ALCOHOLS AND MERCURIC TRIFLUOROACETATE
J. Wasiak et al., PHOSPHORIC-CARBOXYLIC ANHYDRIDES - NEW SYNTHETIC PROCEDURES AND REACTIONS WITH NUCLEOPHILES - REEXAMINATION OF THE REACTION OF SE-ALKYL-PHOSPHOROSELENOATES WITH ALCOHOLS AND MERCURIC TRIFLUOROACETATE, Polish Journal of Chemistry, 69(7), 1995, pp. 1027-1032
Phosphorus trimethylsilyl esters KR'P(O)OSiMe(3) react smoothly with c
arboxylic anhydrides to give phosphoric-carboxylic anhydrides RR'P(O)-
O-COR'' in excellent yield. A similar reaction proceeds between stanny
l esters RR'P(O)OSnMe(3) 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 a
llowed to react with trifluoroacetic anhydride in the presence of N-me
thylimidazole. We were able to confirm again that acyclic phosphoric-c
arboxylic anhydrides exhibit acetylating properties towards amines and
alcohols. Our findings contradict with those of Wozniak, Krzyzanowska
and Stec [6] relating to the reaction of Se-alkylphosphoro-selenoates
RR'P(O)SBR'' with mercuric trirluoroacetate Hg(OCOCF3)(2). Our interp
retation of this reaction differs entirely From those presented by the
above mentioned authors.