3585-88-4

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 2646, 1992 DOI: 10.1021/jo00035a020

InChI:InChI=1/C11H14N2O3/c1-11(2,3)12(14)8-9-4-6-10(7-5-9)13(15)16/h4-8H,1-3H3/b12-8+

Upstream product

• 26378-36-9 2-tert-butyl-3-(4-nitrophenyl)-1,2-oxaziridine 
• 16649-50-6 N-tert-Butylhydroxylamine 
• 555-16-8 4-nitrobenzaldehdye 
• 59862-75-8 (E)-2-methyl-N-(4-nitrophenylmethylene)propan-2-amine 
• 917-95-3 t-butylnitrite 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 718-36-5 (p-nitrobenzylidene)(tert-butyl)amine 
• 3489-67-6 N-(t-butyl)-N-p-nitrobenzylamine 
• 75-18-3 dimethylsulfide 
• 75-64-9 tert-butylamine 
• 57497-39-9 N-tertbutylhydroxylamine hydrochloride 

Downstream Products

• 135485-67-5 C₁₈H₁₉N₂O₅ 
• 63710-80-5 C₁₇H₁₉N₂O₃ 
• 26378-36-9 2-tert-butyl-3-(4-nitrophenyl)-1,2-oxaziridine 
• 555-16-8 4-nitrobenzaldehdye 
• 137578-02-0 C₁₁H₁₅N₂O₄ 
• 52884-61-4 C₁₁H₁₅N₂O₃ 
• 51284-86-7 C₁₇H₁₈N₃O₅ 
• 24393-61-1 ethyl (E)-3-(4-nitrophenyl)-2-propenoate 

Relevant academic research and scientific papers

Single-Step Approach toward Nitrones via Pyridinium Ylides: The DMAP-Catalyzed Reaction of Benzyl Halides with Nitrosoarenes

A single-step approach is reported for the preparation of nitrones from benzyl halides and nitrosoarenes via pyridinium ylides, utilizing 4-dimethylaminopyridine (DMAP) catalyst and mild reaction conditions (Li2CO3, dimethylacetamide, and room temperature). The reaction provides both keto-and aldonitrones in high yields with a wide scope for benzyl halides and nitrosoarenes. In the same reaction system, 2-methyl-2-nitrosopropane, which does not have an aryl group, also affords the corresponding N-tert-butyl nitrones from primary benzyl bromides that have an electron-withdrawing group. As an application of the reaction, methyl 2-bromo-2-phenylacetate was used to prepare the corresponding isoxazolidine by a sequential one-pot synthesis.

Nafion supported molybdenum oxychloride: Recyclable catalyst for one-pot synthesis of nitrones via direct condensation/oxidation of primary amines and aldehydes using UHP as oxidant

Immobilization of molybdenum(vi) oxychloride to the surface of perfluorinated ion-exchange polymer "Nafion"via an ion exchange method was carried out for the first time. The prepared Nafion immobilized molybdenum(vi) oxychloride catalyst was used for the direct synthesis of nitrones via one-pot condensation/oxidation of primary amines with aldehydes using solid urea-hydrogen peroxide (UHP) as oxidant under very mild reaction conditions. The developed polymer immobilized catalyst showed better activity than its analogous homogeneous catalyst with the added benefits of facile recovery and recyclability of the catalyst without leaching and loss in catalytic activity.

Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines

Microwave irradiation allows increasing the speed of several reactions and also offers the possibility of eliminating poisoning organic solvents. In this work we report the microwave-assisted neat synthesis of α-phenyl-tert-butylnitrone (PBN) and other alkyl and aryl nitrones and also the rapid synthesis of isoxazolidines resulting from 1,3-dipolar cycloaddition of nitrones to ethyl trans-crotonate.

α-Phenyl-N-tert-butyl nitrone (PBN) derivatives: Synthesis and protective action against microvascular damages induced by ischemia/reperfusion

Nitrones 4-7, structurally related to PBN (1), were prepared by reaction of the corresponding aromatic aldehydes with N-tert-butyl hydroxylamine. The protective effects of these nitrones against microvascular damages in ischemia/reperfusion in the 'hamste

A novel route to substituted 4-methylene-4,5-dihydroisoxazoles mediated by hafnium(IV) chloride

Heating alkyl vinyl ketones and N-tert-butylarylmethylide-neamine N-oxides in the presence of HfCl4 results in the formation of 4-methylene-4,5-dihydroisoxazoles in good yield.

Oxidation of sulfides to sulfoxides with 3-aryl-2-tert-butyloxaziridines under high pressure

3-Phenyl-2-tert-butyloxaziridine has been shown to behave as an oxidant under 800 MPa at 100°C to oxidize sulfides to sulfoxides, in spite of having been reported to be inactive as an oxidant and to undergo thermal rearrangement to W-tert-butyl-α-phenylnitrone at atmospheric pressure. It has been shown that under thermal and high-pressure conditions the ability of the oxaziridine to react changes dramatically. The mechanism for the high-pressure reaction is also discussed.

Synthesis and Characterization of Phenyl-Substituted C-Phenyl-N-tert-butylnitrones and Some of Their Radical Adducts

Synthesis of C-phenyl-N-tert-butylnitrone (PBN) and several of its analogues with substituents in the 2-, 3-, or 4-position on the phenyl ring is described.While a one-pot reduction/condensation method proved suitable for the most compounds, it was necessary to prepare some examples by direct condensation or through oxidation of the appropriate imine.The 1H NMR data for the 3-X- and 4-X-PBN's can be correlated with the Hammett equation.For the 3-X series Δδ for the α-proton correlates best with ?+ and has a correlation coefficient of 0.90.For the 4-X series a dual substituent parameter equation using ?R0 gives the best correlation with r = 0.99.The hyperfine splitting constants (hfsc's) of HO and HOO adducts of serveral substituted PBN's are also included and their correlation with the Hammett equation is discussed.

Rearrangement Reactions of Oxaziridines to Nitrones. X-Ray Crystal and Molecular Structure of N-t-Butyl-α(o-hydroxyphenyl)nitrone

Substituted N-benzylidene-t-butylamines are oxidized with m-chloroperoxybenzoic acid to oxaziridines which can rearrange to the corresponding nitrones when electron-donating groups are present in the phenyl ring.The oxaziridine-to-nitrone rearrangement, which has been considered as a 'pseudo-abnormal' reaction, can also be catalysed by Lewis acids.It has been found that the rearrangement of 2-t-butyl-3-(o-hydroxyphenyl)oxaziridine to the corresponding nitrone is of first order.The rearrangement has been investigated for different substituents in the phenyl ring, andin the case of 2-t-butyl-3-phenyloxaziridine substituted in the ortho position with electron-donating groups it has been found that the presence of protons of a Lewis acid is necessary.An X-ray structure of α-(o-hydroxyphenyl)-N-t-butylnitrone shows strong hydrogen bonding between the nitrone oxygen and the hydrogen in the hydroxy group.The oxaziridine-to-nitrone rearrangement is also analysed from a theoretical point of view using ab initio calculations.A Mulliken-population analysis of the C-O and N-O bonds in the oxaziridine ring for para-substitued 2-t-butyl-3-phenyloxaziridines shows a reduction of the C-O bond population when an electron-donating group is present in the para position of the phenyl ring compared with an electron-withdrawing group; the N-O bond populations show the reverse picture.A state-correlation diagram for the oxaziridine-to-nitrone rearrangement is also presented and the experimental and theoretical results support each other.

Imines and Derivatives. Part 24. Nitrone Synthesis by Imine Oxidation using either a Peroxyacid or Dimethyldioxirane

The oxidation of N-alkyl imines by m-chloroperoxybenzoic acid to yield nitrones was facilitated by (i) the presence of C-aryl substituents, (ii) steric inhibition of attack at the imino C-atom, (iii) electron donating para-substituents on the C-aryl substituent, (iv) non-hydroxylic solvents, (v) optimal conjugation between C-aryl substituents and the imino group, and (vi) less bulky N-alkyl groups. The oxidation of N-alkyl imines by dimethyldioxirane (DMD) in dichloromethane-acetone solution yielded nitrones without evidence of oxaziridine formation.The yields of isolated nitrones were higher for C,C-diaryl imines and for imines bearing less bulky N-alkyl substituents.N-H substituted ketimines were found to yield oximes after reaction with dimethyldioxirane.