74635-18-0

Upstream product

• 50-00-0 formaldehyd 
• 622-30-0 N-benzyl hydroxylalmine 
• 3555-72-4 N-benzyl-N-methylhydroxylamine 
• 103-67-3 benzyl-methyl-amine 
• 29601-98-7 N-benzylhydroxylamine hydrochloride 

Downstream Products

• 133957-73-0 N-[(R)-1-((S)-2-Benzyl-isoxazolidin-5-yl)-ethyl]-benzamide 
• 160823-80-3 (3aS,3bR,6R,7aR)-2-benzyl-1,2,3a,3b,4,7a-hexahydro-6-phenyl-3,5-dioxa-2,6a-diazacyclopentapentalen-7-one 
• 169478-04-0 (2R,5S,6S)-6-(N-benzyl-N-hydroxy)amino-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane-8-one 
• 162826-90-6 (4R,7R,8S)-2-benzyl-7-hydroxymethyl-6-methoxycarbonyl-1-oxa-2,6-diazabicyclo<3.3.0>octane-5-one 

Relevant academic research and scientific papers

The importance of electrostatic interactions in the stereoselective 1,3-dipolar cycloadditions of nitrones to chiral allyl ethers: An experimental and force field approach

The 1,3-dipolar cycloaddition of formaldehyde N-benzylnitrone with β′-alkoxy- and γ-alkoxy-α,β-unsaturated esters was investigated. The stereochemical outcome of these reactions was nicely rationalized on the basis of an interpretation of the inside alkox

(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route t

Direct and Co-catalytic Oxidation of Hydroxylamines to Nitrones Promoted by Rhodium Nanoparticles Supported on Carbon Nanotubes

Rhodium nanoparticles were assembled on carbon nanotubes, and the resulting nanohybrid was studied in the aerobic oxidation of hydroxylamines to nitrones. Two catalytic systems were developed (i.e., direct or co-catalytic) and both operated to provide high yields of the products, under mild conditions, but with their own specificity as regards the kinetics and regioselectivity of the transformation. In addition, the in situ cycloaddition of the produced nitrones with different alkynes was investigated.

The nitrogen inversion in fused isoxazolidinyl derivatives of substituted uracil: synthesis, NMR and computational analysis

A series of fused isoxazolidines have been prepared via 1,3-dipolar cycloaddition reactions of N-protected methylenenitrones with 1,3-dimethyluracil derivatives, and their NMR spectra have been recorded in TFA-d and in CDCl3 over a wide range of temperatures. The spectra indicate the presence of two invertomers for all isoxazolidines. Barriers to nitrogen inversion in the cycloadduct 6a have been determined using DFT quantochemical calculations. Our estimates have shown that the inversion proceeds at more complex path, involving four structures of local minima and four transition states.

Organocatalytic asymmetric synthesis of versatile γ-lactams

A goodstarting point: Optically pure glactams have been prepared by organocatalytic enantioselective vinylic substitution. The parent lactam structure allows logical and systematic introduction of functionality around the periphery to access new derivativ

Oxidation of secondary amines by molecular oxygen and cyclohexanone monooxygenase

Cyclohexanone monooxygenase from Acinetobacter calcoaceticus catalyzed the oxidation of tertiary and secondary amines to N-oxides and nitrones, respectively. The formation of a hydroxylamine intermediate was involved with secondary amines as starting substrates.

Oxidation of amines catalyzed by cyclohexanone monooxygenase

Cyclohexanone monooxygenase catalyzed the oxidation of tertiary, secondary and hydroxylamines to N-oxides, hydroxylamines and nitrones respectively.

Regiochemistry and mechanism of oxidation of N-benzyl-N-alkylhydroxylamines to nitrones

The oxidation of various N-(o-, m-, p-substituted benzyl)-N-alkylhydroxylamines and their dideuteriobenzyl (PhCD2) counterparts was carried out using mercury(II) oxide and p-benzoquinone (p-BQ) as oxidants. An overwhelming preference for the formation of conjugated nitrones is observed in the oxidation of N-benzyl-N-isopropylhydroxylamines. Considerable intra- and intermolecular kinetic isotope effects and negative ρ values in the Hammet plots point towards a mechanistic pathway that involves electron transfer from nitrogen to the oxidant followed by hydrogen abstraction. The conformation of unstable (E)-nitrones, which readily isomerize to the more stable (Z)-nitrones, is deduced from 1H NMR data. The E ? Z isomerization was found to be a bimolecular process. Copyright

Oxidation of N-benzyl-N-methylhydroxylamines to nitrones. A mechanistic study

Oxidation of various N-(o-, m-, p- substituted benzyl)- N-methylhydroxylamines has been carried out using mercury(II) oxide and p-benzoquinone (p-BQ) as oxidants. Hammett plots have been obtained with negative ρ values, showing the development of a positive centre in the transition state. The unstable E nitrones, which readily isomerize to the more stable Z nitrones, are obtained in appreciable quantities and in some cases as the major product. A considerable deuterium isotope effect is observed in the oxidation process. The overall picture of the mechanistic pathway involves electron transfer from nitrogen to the oxidant followed by hydrogen abstraction.

Regiochemistry of mercury(II) oxide oxidation of unsymmetrical N,N-disubstituted hydroxylamines

Mercury(II) oxide oxidation of N,N-disubstituted hydroxylamines with the α and α' carbon atoms containing one and two hydrogen atoms, respectively, gave aldonitrones in a highly regioselective manner. Removal of the α proton is involved in the rate determining step as shown by primary kinetic isotope effect.