68883-38-5

Upstream product

• 3376-24-7 N-tert-butyl-α-phenylnitrone 
• 3378-72-1 N-tert-butylbenzylamine 
• 3376-24-7 (Z)-N-benzylidene-2-methylpropan-2-amine oxide 
• 16649-50-6 N-tert-Butylhydroxylamine 
• 100-52-7 benzaldehyde 
• 6852-58-0 N-benzylidene tert-butylamine 
• 3585-81-7 2-tert-butyl-3-phenyloxaziridine 

Downstream Products

• 24293-08-1 N-tert-butyl-N-benzylnitroxyl 
• 3376-24-7 N-tert-butyl-α-phenylnitrone 

Relevant academic research and scientific papers

Selective Oxidation of Secondary Amines to N,N-Disubstituted Hydroxylamines by Choline Peroxydisulfate

N,N-Disubstituted hydroxylamines were prepared directly from secondary amines by a reliable method using an oxidizing task-specific ionic liquid, choline peroxydisulfate. The operational simplicity, high selectivity, and green reaction conditions, make this method efficient and practical.

O-trifluoromethylation of N,N-disubstituted hydroxylamines with hypervalent iodine reagents

A mild trifluoromethylation reaction of N,N-disubstituted hydroxylamines that is tolerant towards a variety of functional groups, including nitriles, alcohols, ketones, esters, amides, imides, and nitrogen heterocycles, is reported. The key feature of this reaction is the activation of the CF 3 reagent with either trimethylsilyl triflate or LiClO4 and partial or full deprotonation of the substrate with tetramethylguanidine or lithium diisopropylamide. Products were obtained in up to 80 % yield. Preliminary mechanistic studies suggested that the reaction follows a radical pathway in which the deprotonated hydroxylamine and a Lewis or Bronsted acid activated CF3 reagent engages in a single-electron-transfer step to generate a pair of radicals that recombine to afford the desired product. The trifluoromethylation procedure was successfully used in the modification of secondary nitrogen groups of pharmaceutically relevant targets (Fluoxetine and Mefloquine), which afforded new derivatives containing a novel N-trifluoromethoxy moiety. Copyright

Methyltrioxorhenium-catalysed oxidation of secondary amines to nitrones in ionic liquids

Nitrones serve as starting materials for the synthesis of many heterocycles. Oxidation of secondary amines using hydrogen peroxide and the catalytic amount of methyltrioxorhenium in ionic liquids is a useful method for the preparation of nitrones. Ultrasonic irradiation and ionic liquids have a positive influence on the reaction. The nitrones required were isolated in good yields. Corresponding hydroxylamines, which can be easily oxidised to nitrones, often accompanied the main products. Methyltrioxorhenium in ionic liquids was re-used in several reaction cycles without any deteriorating effect on the course of the reaction.

Nitrogen inversion and N-O bond rotation in some hydroxylamine and isoxazolidine derivatives

A series of trisubstituted hydroxylamine derivatives, both cyclic and acyclic, has been prepared. The energy barriers in these hydroxylamines are found to be dominated either by nitrogen inversion or N-O bond rotation depending on the nature of the substi

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.

Synthesis of hydroxylamines using dioxiranes

The subject invention relates to a method of synthesizing hydroxylamines from secondary amines. This method uses a dioxirane compound such as dimethyldioxirane (DMD, which is relatively stable and simple to synthesize), as the oxidizing agent. The reaction proceeds as follows: STR1 This method provides a simple, one-step reaction with high yields. It can be performed in acetone solution, and the transferral of an oxygen atom from dimethyldioxirane to the secondary amine converts the dioxirane into acetone, the solvent, permitting simple workup and purification. This method can be used with a wide variety of secondary amines, including aliphatic, aromatic, cyclic, and heterocyclic secondary amines, to create a corresponding variety of hydroxylamines.

1H NMR of (α-Substituted benzyl-t-butyl)hydroxylamines and EPR of Their Oxidized Forms

1H NMR study of several (benzyl-t-butyl)hydroxylamine derivatives (BBHA) was performed, which were obtained through the addition of Grignard agents to α-phenyl-N-t-butylnitrone (PBN) or the reduction of PBN.Concominantly, EPR of their oxidized forms (nitr

A HIGH YIELD ONE STEP SYNTHESIS OF HYDROXYLAMINES

Oxidation of secondary amines with dimethyldioxirane gives hydroxylamines in a simple, one step and high yield process.