14397-53-6

Upstream product

• 95-92-1 oxalic acid diethyl ester 
• 79-37-8 oxalyl dichloride 
• 108-18-9 diisopropylamine 
• 110193-57-2 methyl 2-(diisopropylamino)-2-oxoacetate 
• 201230-82-2 carbon monoxide 
• 104189-31-3 2-[bis(1-methylethyl)amino]-2-oxoacetic acid 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 100-48-1 pyridine-4-carbonitrile 

Downstream Products

• 96323-94-3 N,N,N',N'-Tetraisopropyl-oxalamide; compound with o-xylene 
• 96323-96-5 N,N,N',N'-Tetraisopropyl-oxalamide; compound with p-xylene 
• 96323-95-4 N,N,N',N'-Tetraisopropyl-oxalamide; compound with m-xylene 
• 96323-93-2 N,N,N',N'-Tetraisopropyl-oxalamide; compound with toluene 
• 96345-72-1 N,N,N',N'-Tetraisopropyl-oxalamide; compound with benzene 
• 96324-03-7 N,N,N',N'-Tetraisopropyl-oxalamide; compound with benzene-1,3-diol 
• 96323-99-8 N,N,N',N'-Tetraisopropyl-oxalamide; compound with 4-methyl-phenol 

Relevant academic research and scientific papers

On the two-ligand catalytic asymmetric deprotonation of N-Boc pyrrolidine: Probing the effect of the stoichiometric ligand

(Chemical Equation Presented) To map out the stoichiometric ligand requirements in the two-ligand catalytic asymmetric deprotonation of N-Boc pyrrolidine, 24 different ligands have been evaluated; the highest enantioselectivity (90:10 er) was obtained by using s-BuLi in the presence of 0.3 equiv of (-)-sparteine and 1.3 equiv of a cyclohexanediamine-derived ligand.

Selective oxidative carbonylation of amines to oxamides and ureas catalyzed by palladium complexes

A new process for converting secondary amines into N,N,N′,N′- tetraalkyloxamides under CO pressure, catalyzed by homogeneous palladium complexes in the presence of 1,4-dichloro-2-butene (DCB) as an oxidant, has been developed. The mechanism of the oxidative double-carbonylation process, consisting of the oxidation of Pd(0) to Pd(11) with DCB through a β-chloride elimination of the η3-(chloromethyl) allylpalladiuni(11) intermediate, the formation of mono- and bis(carbamoyl)palladium species, and a reductive elimination of the two carbamoyl ligands, is proposed based on studies of the behavior of carbamoylpalladium complexes. When primary amines are employed with DCB as the oxidant, N,N′-dialkyloxamide is catalytically produced, whereas urea is exclusively produced when iodine is used as the oxidant. The reaction of an N-monopropylcarbamoylpalladium complex with propylamine under CO gave N,N′-dipropylurea, whereas a treatment with diethylamine yielded unsymmetrical N,N-diethyl-N′-propylurea, implying the intermediate formation of propyl isocyanate that is converted into the urea upon a reaction with the added amine. A kinetic study on the reaction of chloro-N- propylcarbamoylpalladium with triethylamine suggested a process proceeding through a base-promoted dcprolonalion of the N-monoalkylcarbamoyl ligand to form propyl isocyanate.

A FACILE, CONVENIENT AND SELECTIVE HOMOLYTIC CARBAMOYLATION OF HETEROAROMATIC BASES

The oxidative decarboxylation of monoamides of oxalic acid provides carbamoyl radicals, which are useful for the selective carbamoylation of protonated heteroaromatic bases; this reaction represents the first general and selective method for the N-alkyl or N-arylcarbamoylation of heteroaromatic bases.Compared to alkoxycarbonylation, this reaction is much more effective and selective, owing to more favourable polar and enthalpic effects.The importance of the steric effects is also emphasized.

Alkylation of Aromatic Heterocycles with Oxalic Acid Monoalkyl Esters in the Presence of Trivalent Iodine Compounds

Aromatic heterocycles containing nitrogen atoms were easily alkylated with the half esters of oxalic acid, which were prepared from alcohols, in the presence of benzene via radical decarboxylative pathways.This is the first method for the alkylation of aromatic heterocycles with alcohols via the formation of half esters of oxalic acid.