10049-90-8Relevant articles and documents
Barbier Continuous Flow Preparation and Reactions of Carbamoyllithiums for Nucleophilic Amidation
Ganiek, Maximilian A.,Becker, Matthias R.,Berionni, Guillaume,Zipse, Hendrik,Knochel, Paul
supporting information, p. 10280 - 10284 (2017/08/07)
An ambient temperature continuous flow method for nucleophilic amidation and thioamidation is described. Deprotonation of formamides by lithium diisopropylamine (LDA) affords carbamoyllithium intermediates that are quenched in situ with various electrophi
Carbmoyllithiums. A Novel Method for Generation by Lithium-Tellurium Exchange Reaction
Hiiro, Tomoki,Mogami, Toshiaki,Kambe, Nobuaki,Fujiwara, Shin-Ichi,Sonoda, Noboru
, p. 703 - 711 (2007/10/02)
Reaction of Te-butyl carbamotelluroates with butyllithium at low temperatures resulted in efficient transmetallation to give corresponding carbamoyllithiums.A convenient one-pot procedure for nucleophilic carbamoylation using carbamoyl halides has been developed as an application of this reaction.
Electrogenerated Bases. VI. Reaction of Electrogenerated Superoxide with Some Carbon Acids. II.
Sugawara, M.,Baizer, M. M.,Monte, W. T.,Little, R. D.,Hess, U.
, p. 509 - 518 (2007/10/02)
Electrogenerated superoxide and molecular oxygen were allowed to react sequentially with a number of esters, nitriles, N,N-dialkylamides, sulfones, and aliphatic nitro compounds.The α-methyl groups in these compounds bore aliphatic and/or aromatic substituents.When the electron-withdrawing group (EWG) of these carbon acids could be displaced intact (nitile 2, ArSO2 4, nitro) good to excellent yields of the corresponding carbonyl compounds could be obtained.The efficiency of the transformation depended upon the nature of the substituents: α,α-diphenyl (e.g., 2a) > α-methyl-α-phenyl (2b) > α,α-dimethyl.By conducting the electrolysis in the presence of acetic anhydride it was shown that the known conversion of phenylacetonitrile (2d) to benzoic acid did indeed proceed via benzaldehyde.When the EWG itself could be cleaved (esters 1, N,N-dialkyl-amides 3), this methodology produced α-hydroxylated compounds and the products resulting from fragmentation of the EWG and also from its complete displacement.The effects of the α-substituents were similar to those above.