82044-40-4

Upstream product

• 943-72-6 (p-chlorobenzylidene)(tert-butyl)amine 
• 86402-00-8 (E)-N-tert-butyl-1-(4-chlorophenyl)methanimine 
• 104-88-1 4-chlorobenzaldehyde 
• 75-64-9 tert-butylamine 

Downstream Products

• 42498-40-8 N-tert-butyl-4-chlorobenzamide 
• 5894-65-5 N-t-butylbenzamide 
• 40117-30-4 N-<(4-Chlorophenyl)methylene>-2-methyl-2-propanamine N-Oxide 

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.

[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.

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.

PHASE-TRANSFER CATALYTIC SYNTHESIS OF OXAZIRIDINES

The phase-transfer catalytic oxidation of imines is a general method for the preparation of oxaziridines with various structures.Oxone (2KHSO5*KHSO4*K2SO4) and perbenzoic acid in combination with such phase-transfer catalysts as benzyltriethylammonium chl

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.

Synthesis of 2-Alkyl-3-aryloxaziridines

A convenient method for the synthesis of 2-alkyl-3-aryloxaziridines 1 based on the formation of stable azomethines and their oxidation with m-chloroperoxybenzoic acid is reported.The scope and limitation of the method proposed is illustrated with numerous

NORMAL, ABNORMAL AND PSEUDO-ABNORMAL REACTION PATHWAYS FOR THE IMINE-PEROXYACID REACTION

Steric and mesomeric effects have a marked influence upon the formation of oxaziridine (normal pathway) or nitrone (abnormal pathway) products from the imine-peroxyacid reaction; n.m.r. studies of the thermal isomerization of oxaziridines to nitrones prov