96018-73-4

Upstream product

• 50-00-0 formaldehyd 
• 3623-23-2 4-bromonitrosobenzene 
• 298-12-4 Glyoxilic acid 
• 563-96-2 2,2-dihydroxyacetic acid 
• 106-40-1 4-bromo-aniline 
• 10468-46-9 N-(4-bromophenyl)hydroxylamine 
• 2258-42-6 formyl acetic anhydride 

Relevant academic research and scientific papers

Transketolase Catalyzed Synthesis of N-Aryl Hydroxamic Acids

Hydroxamic acids are metal-chelating compounds that show important biological activity including anti-tumor effects. We have recently engineered the transketolase from Geobacillus stearothermopilus (TKgst) to convert benzaldehyde as a non-natur

Formation of hydroxamic acids promoted by metal ions. Interaction of aldehyde carbonyl group with C-nitroso group in the presence of ferric ions

Formation of N-phenyl substituted hydroxamic acids in the reaction of formaldehyde with substituted nitrosobenzene is strongly catalysed by Fe3+ ions, which stabilize the transition state for the rate-controlling proton transfer from the carbon of nitrosocarbinolic cation intermediate leading to the product, hydroxamic acid.

Reactions of Carbonyl Group with Nitroso Compounds: Reaction of Formaldehyde with Substituted Nitrosobenzenes

Formaldehyde reacts with substituted nitrosobenzenes giving the corresponding N-phenylhydroxamic acids.A mechanism involving three sequential steps in this reaction is proposed.The first step is the nucleophilic attack of the nitroso group on the carbonyl group which leads to the formation of the unstable tetrahedral zwitterionic intermediate.This step followed by the proton transfer to the zwitterionic intermediate to form more stable nitrosocarbinolic cation intermediate, which in the subsequent step undergoes the rate-controlling elimination of proton from the C-atom of nitrosocarbinolic group, leading to the final product, hydroxamic acid.The first and the second step appear to be reversible.The experimental evidence obtained, which is the basis for such a description of the investigated reaction, includes: a) the order of reactivity of substituted nitrosobenzenes, as demonstrated by the plot of log kobs vs. ? Hammett parameters with slope of -1.74; b) the observation of a general-acid catalysis; c) the observation of the inverse solvent deuterium isotope effect of ca. 1.8 in the reaction; d) the observation of kinetic primary deuterium isotope effect of ca. 8 related to to the 'water' reactions of formaldehyde with substituted nitrosobenzenes; e) the observation of general-base catalysis in the reaction; f) the observation of the kinetic primary deuterium isotope effect of ca. 2.1 for the acetate-ion catalyzed reaction.

A facile synthesis of N-aryl-N-hydroxyformamides from N-arylhydroxylamines

Several N-arylhydroxylamines (2) have been formylated for the first time with acetic formic anhydride to yield N-hydroxyformanilides (3) in better yields than hitherto reported.

Reaction of Substituted Nitrosobenzenes with Formaldehyde

Substituted nitrosobenzenes react with formaldehyde in an acid-catalysed reaction giving N-phenylhydroxamic acids.

Reaction of Nitroso Aromatics with Glyoxylic Acid. A New Path to Hydroxamic Acids

In aqueous solution substituted aromatic nitroso compounds react rapidly with glyoxylic acid to produce N-hydroxyformanilides and CO2.The reaction is nearly quantitative for all nitroso aromatics investigated and serves as a convenient synthetic route to