4693-63-4Relevant academic research and scientific papers
Direct conversion of carboxylic acids to various nitrogen-containing compounds in the one-pot exploiting curtius rearrangement
Kumar, Arun,Kumar, Naveen,Sharma, Ritika,Bhargava, Gaurav,Mahajan, Dinesh
, p. 11323 - 11334 (2019/09/10)
Herein we report, a single-pot multistep conversion of inactivated carboxylic acids to various N-containing compounds using a common synthetic methodology. The developed methodology rendered the use of carboxylic acids as a direct surrogate of primary amines, for the synthesis of primary ureas, secondary/tertiary ureas, O/S-carbamates, benzoyl ureas, amides, and N-formyls, exploiting the Curtius reaction. This approach has a potential to provide a diversified library of N-containing compounds, starting from a single carboxylic acid, based on the selection of the nucleophile.
Synthesis and Stabilization of (Benzoyl- and Pentafluorobenzoyloxy)diphenylphosphane and Comparison with the Corresponding Isomeric Aroyldiphenylphosphane Oxides
Lindner, Ekkehard,Wuhrmann, Juan Carlos
, p. 297 - 300 (2007/10/02)
(Benzoyloxy)- and (pentafluorobenzoyloxy)diphenylphosphanes RC(O)OPPh2 (2a,b) can be obtained by reaction of ClPPh2 (1) with NaO2CC6H5 and AgO2CC6F5, respectively .Oxidation of 2a with molecular oxygen yields (benzoyloxy)d
Solvation and Catalysis in Displacement at Phosphorus. Reaction of Imidazole and Benzoate Ion with p-Nitrophenyl and 2,4-Dinitrophenyl Diphenylphosphinates
Wallerberg, Gun,Haake, Paul
, p. 43 - 46 (2007/10/02)
The reactions of two phosphorus esters, p-nitrophenyl diphenylphosphinate (I) and 2,4-dinitrophenyl diphenylphosphinate (II), have been investigated in acetonitrile containing variable amounts of water.The effectiveness of imidazole and benzoate ion as catalysts has been investigated.Whereas the reaction of imidazole with II is quite rapid, the reaction with I is very slow.However, I reacts predominantly by the rate term k and shows no k term.Nucleophilic catalysis and the existence of an anhydride intermediate have been confirmed with I by observation of the carbonyl region in the infrared: a C=O peak appropriate for an anhydride appears with C6H5CO2(1-) and then disappears if imidazole is added.This correlates with kinetic evidence for an equilibrium with benzoate ion alone but complete reaction if benzoate and imidazole are both present.The reaction of II has been shown to proceed by reversible formation of 1-(diphenylphosphinyl)imidazole as an intermediate.
Phosphorylation with N-Phosphorylpyrazoles, IV. - Phosphorylations of Carboxylic Acids
Regitz, Manfred,Weise, Gisela,Felcht, Utz
, p. 1232 - 1238 (2007/10/02)
Reaction of 1-phosphorylpyrazole (1a) with the carboxylic acids 5a-f leads initially to the mixed anhydrides 6a-f, which then transform the 1-H-pyrazole 3, arising from phosphoryl group transfer, into the 1-acylpyrazoles 7a-f.Carboxylic acid phosphinic acid anhydrides 6b, c and g-k are also formed on reaction of the phosphinic acid chloride 9 and carboxylic acids in the presence of triethylamine; acylation of 3 with 6b, c, i and k is described.
