26378-36-9

Usage

Synthesis Reference(s)

Tetrahedron, 44, p. 6821, 1988 DOI: 10.1016/S0040-4020(01)86210-4

Upstream product

• 3585-88-4 (Z)-N-tert-butyl-1-(4-nitrophenyl)methanimine oxide 
• 59862-75-8 (E)-2-methyl-N-(4-nitrophenylmethylene)propan-2-amine 
• 576-26-1 2.6-dimethylphenol 
• 3585-88-4 N-tert-butyl-α-(4-nitrophenyl)nitrone 
• 555-16-8 4-nitrobenzaldehdye 
• 75-64-9 tert-butylamine 
• 718-36-5 (p-nitrobenzylidene)(tert-butyl)amine 

Downstream Products

• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 2455-14-3 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone 
• 555-16-8 4-nitrobenzaldehdye 
• 88343-92-4 2,6-Di-tert-butyl-4-[hydroxy-(4-nitro-phenyl)-methyl]-phenol 
• 1988-11-0 2,6-diisopropyl-1,4-benzoquinone 
• 718-36-5 (p-nitrobenzylidene)(tert-butyl)amine 
• 3585-88-4 (Z)-N-tert-butyl-1-(4-nitrophenyl)methanimine oxide 
• 3585-88-4 N-tert-butyl-α-(4-nitrophenyl)nitrone 
• 527-61-7 2,6-dimethyl-1,4-benzoquinone 
• 67-68-5 dimethyl sulfoxide 
• 77621-69-3 C₃₅H₄₇NO₄ 
• 42498-30-6 N-tert-butyl-4-nitrobenzamide 

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.

Hydrogen peroxide/dimethyl carbonate: A green system for epoxidation of: N -alkylimines and N -sulfonylimines. One-pot synthesis of N -alkyloxaziridines from N -alkylamines and (hetero)aromatic aldehydes

A green method for epoxidation of imines using an environmentally benign oxidant system, H2O2/dimethyl carbonate, was developed. N-Alkyloxaziridines were prepared in high yields from N-alkylamines and (hetero)aromatic aldehydes in one-pot fashion, whereas N-sulfonyloxaziridines have been prepared by using the same oxidant system and 5 mol% of Zn(OAc)2·2H2O as catalyst.

UV-vis monitoring of radical polymerizations by spin trapping with chromophoric nitrones

The application of chromophoric radical spin traps for highly sensitive UV-vis monitoring of conversion of radical enhanced spin capturing polymerizations (ESCP) is presented. In ESCP the growing macroradical is reacting with a nitrone providing the corresponding polymeric nitroxide radical spin trap which will react irreversibly with a second macroradical to eventually give a polymeric alkoxyamine. The progress of styrene and n-butyl acrylate ESC polymerizations in the presence of π-conjugated nitrones is successfully visualized via a significant change of absorbance of the nitrone chromophore in the 200-500 nm range due to the nitrone transformation into an alkoxyamine moiety upon incorporation into the polymer. Moreover, related studies on UV-vis monitoring of photochemical rearrangement of nitrones to their corresponding oxaziridines are discussed.

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.

trans-(±)-2-tert-butyl-3-phenyloxaziridine: A unique reagent for the oxidation of thiolates into sulfenates

(Chemical Equation Presented) Aliphatic thiolates were efficiently converted into the corresponding sulfenates by smooth oxidation with trans-(±)-2-tert-butyl-3-phenyloxaziridine at room temperature (five examples). Subsequent electrophilic quench with benzyl bromide led to sulfoxides (S-alkylation) in good to moderate yields. Application of the protocol to an aromatic substrate was also successful. This work represents the first valuable example of the use of this poorly active oxidizing agent in synthetic organic chemistry without the need for activating conditions.

[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.

An inexpensive and selective oxygenation of N-alkyl imines to oxaziridines

A range of N-alkyl imines was oxidised to corresponding oxaziridines in a highly selective manner with sodium tungstate-30% H2O2 in acetonitrile under mild conditions.

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.