82079-47-8

Upstream product

• 15875-74-8 N-(4-methoxybenzylidene)-2-methylpropan-2-amine 
• 123-11-5 4-methoxy-benzaldehyde 
• 75-64-9 tert-butylamine 
• 15875-74-8 (E)-tert-butyl[(4-methoxyphenyl)methylidene]amine 

Downstream Products

• 1253786-06-9 2-tert-butyl-3-(4-methoxyphenyl)-2,3-dihydrobenzo[d]isoxazole 
• 1253786-19-4 2-tert-butyl-3-(4-methoxyphenyl)-5,6-dimethyl-2,3-dihydrobenzo[d]isoxazole 
• 1253786-22-9 2-tert-butyl-1-(4-methoxyphenyl)-1,2-dihydronaphtho[1,2-d]isoxazole 
• 19486-73-8 N-tert-butyl-4-methoxybenzamide 
• 1035327-97-9 2-tert-butyl-3-(4-methoxy-phenyl)-5-phenyl-isoxazoline 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 15875-74-8 N-(4-methoxybenzylidene)-2-methylpropan-2-amine 
• 40117-28-0 N-(4-methoxy)benzylidene-t-butylamine N-oxide 
• 123-11-5 4-methoxy-benzaldehyde 

Relevant academic research and scientific papers

Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis

The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.

Atom economical synthesis of: N -alkylbenzamides via the iron(III) sulfate catalyzed rearrangement of 2-alkyl-3-aryloxaziridines in water and in the presence of a surfactant

A green and mild synthetic route to N-alkylbenzamides involves eco-friendly one pot synthesis of 2-alkyl-3-aryloxaziridines from N-alkylamines and benzaldehydes followed by iron(iii) sulfate catalyzed rearrangement to the corresponding amides in water as the solvent and in the presence of sodium dodecyl sulfate as the surfactant. This green approach affords N-alkylbenzamides in high overall yields under simple and minimum manipulation.

Enantio-and diastereoselective oxidation of N-alkylimines using chiral-bromonitriles and hydrogen peroxide system

Chiral-bromonitriles were prepared with good chemical and optical yields starting from natural-amino acids by dehydrating the corresponding α-bromoamides with thionyl chloride. The combined system-bromonitriles/ hydrogen peroxide was examined for the enantio-and diastereoselective oxidation of N-alkylimines in basic media at room temperature. The oxidation of N-tertiobutylarylimines leads to optically active oxaziridines with moderate enantiomeric excess. However, the oxidation of (S)-1-phenylethylarylimines affords the corresponding oxaziridines with good diasteromeric excess up to 97/3 as proved by gaseous-phase chromatography.

Synthesis of dihydrobenzisoxazoles by the [3 + 2] cycloaddition of arynes and oxaziridines

Dihydrobenzisoxazoles are readily prepared in good yields by the [3 + 2] cycloaddition of oxaziridines and arynes. The reaction involves an unusual cleavage of the C-O bond of the oxaziridine and tolerates a variety of substituents on the oxaziridine and the o-(trimethylsilyl)aryl triflate to form aryl-, heteroaryl-, alkyl-, and naphthyl-substituted dihydrobenzisoxazoles. The resulting halogen-substituted dihydrobenzisoxazoles are readily elaborated to more complex products using palladium-catalyzed crossing-coupling processes.

Synthesis of stable isoxazolines by [3+2] cycloaddition of oxaziridines with alkynes

N-Alkyl substituted oxaziridines undergo a [3+2] cycloaddition reaction with a variety of terminal alkynes to give the product isoxazolines, whose stability appears to depend on the electronic properties of the groups on the C-3 and C-5 positions. The presence of an electron withdrawing group on C-5 and/or an electron donating group on C-3 causes isomerization of the isoxazolines to β-amino enones.

[Bmim]BF4-immobilized rhenium-catalyzed highly efficient oxygenation of aldimines to oxaziridines using solid peroxides as oxidants

Various rhenium-based catalysts immobilized in [bmim]BF4 were found to be efficient for oxygenation of various aldimines to the corresponding oxaziridines in excellent yields under mild conditions using solid peroxides like UHP, SPC and SPB as oxidants. Among the various rhenium-based catalysts studied, MTO was found to be most efficient. The reusability and recyclability of MTO immobilized in [bmim]BF4 was established by using it for three subsequent cycles for oxygenation of benzylidine-tert-butylamine using UHP as oxidant.

An environmentally friendly oxidation system for the selective oxygenation of aldimines to oxaziridines with anhydrous TBHP and alumina-supported MoO 3 as a recyclable heterogeneous catalyst

A highly efficient and selective protocol for the oxygenation of various aldimines to oxaziridines, which proceeds in excellent yields with enhanced selectivity by using alumina-supported M0O3 as a recyclable heterogeneous catalyst and anhydrous TBHP as the ultimate oxidant, is described. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Simple and highly efficient synthesis of oxaziridines by tetrabutylammonium Oxone

Oxygenation of various aldimines with tetrabutylammonium monoperoxysulfate produced the corresponding E- or a mixture of E- and Z-oxaziridines with very high yields (≥90%) and good to excellent selectivities (75-100%) within 20min to 10h in CH3CN at room temperature (～25°C). The E/Z isomer ratio critically depends on the stereo-electronic nature of the substituents in the oxaziridines, solvent, and the presence of Lewis acids and bases.

Sulfonic peracids - III. Heteroatom oxidation and chemoselectivity

We have investigated the p-toluenesulfonic peracid (2) generated in situ in the oxidation of different types of compounds containing nitrogen and/or sulfur. The sulfonic peracid 2 shows a remarkable chemoselectivity characterized by a preferred oxidation of sulfides to the sulfones in the presence of amines or olefins and a strong dependence on the nature of the amine in the competitive oxidation of olefins and amines.

Oxidation of Imines to Oxaziridines catalysed by Transition Metal Complexes using Molecular Oxygen as the Terminal Oxidant

The metal-catalysed oxidation of imines using molecular oxygen as the terminal oxidant and aldehydes as co-reductants has been studied.Different transition metal complexes have been tested as catalysts and it is found that cobalt complexes can catalyse the selective oxidation of imines to oxaziridines.The cobalt-catalysed oxidation of imines to oxaziridines is dependent on the aldehyde used as co-reductant; thus, the presence of aliphatic aldehydes leads to a smooth oxidation, whilst in the presence of aromatic aldehydes there was no reaction.The oxidation proceeds well for imines with aliphatic and aromatic substituents attached to the nitrogen and carbon atom, respectively.The electronic nature of the oxygen atom transferred in these reactions, investigated using thianthrene 5-oxide as a probe, was found to be electrophilic in character.The mechanistic aspects of the cobalt-catalysed oxidation of imines to oxaziridines, probably involving a peroxyacyl cobalt intermediate, are discussed.