Monomeric Methyl Metaphosphate: Reactions with Carbonyl Groups

Article abstract of DOI:10.1021/ja00533a027

Monomeric methyl metaphosphate, generated by fragmentation of methyl hydrogen erythro-1-phenyl-1,2-dibromopropylphosphonate in the presence of 2,2,6,6-tetramethylpiperidine, can be identified by its electrophilic attack on the aromatic rings of substituted anilines.The aromatic substitution reactions are quenched by pyridine, acetonitrile, dioxane, and dimethoxyethane but not by chloroform.Monomeric methyl metaphosphate attacks acetophenone to yield an enol phosphate; it converts a mixture of o-trifluoromethylaniline and acetophenone into N-(1-methylbenzylidene)-2-aminobenzotrifluoride and also converts aniline and ethyl benzoate into O-ethyl-N-phenylbenzimidate.These latter reactions mimic enzymatic reactions that require ATP.These facts introduce the possibility that ATP plays a kinetic role as well as a thermodynamic one in metabolic processes.