1016-07-5

Upstream product

• 698-16-8 benzohydroximoyl chloride 
• 110-83-8 cyclohexene 
• 932-90-1 Benzaldoxime 
• 934-16-7 phenylhydroxamoyl chloride 
• 20141-73-5 benzaldehyde oxime O-tributylstannyl ether 
• 695-12-5 vinylcyclohexane 
• 100-52-7 benzaldehyde 
• 873-67-6 benzonitrile oxide 

Downstream Products

• 65395-59-7 2-phenyl-4,5,6,7-tetrahydro-1H-azepine-3-carbaldehyde 
• 65395-62-2 8-phenyl-9-oxa-7-aza-bicyclo[4.2.1]non-7-ene 
• 100-47-0 benzonitrile 

Relevant academic research and scientific papers

Hypervalent iodine-catalyzed cycloaddition of nitrile oxides to alkenes

A new and convenient method for preparation of isoxazolines was developed by a catalytic cycloaddition of nitrile oxides generated in situ from aldoximes to alkenes in the presence of a catalytic amount of iodobenzene. In this protocol, iodobenzene was fi

PhIO promoted synthesis of nitrile imines and nitrile oxides within a micellar core in aqueous media: A regiocontrolled approach to synthesizing densely functionalized pyrazole and isoxazoline derivatives

A highly efficient and general protocol has been developed for the facile synthesis of highly diversified 1,3,5-trisubstituted pyrazoles and 3,5-disubstituted 2-isoxazolines through one-pot tandem intermolecular, as well as intramolecular, dipolar [3 + 2] cycloaddition reactions. Chemoselective oxidation of aldohydrazone to nitrile imine and aldoximes to nitrile oxides by iodosobenzene in neutral aqueous media was performed. The scope of the reactions in regiocontrolled dipolar cycloaddition with olefins in the presence of PhIO toward highly substituted pyrazole and isoxazoline derivatives has been demonstrated. SDS converted the initially floating reaction mass and the organo-oxidant PhIO into a homogeneous mixture, which on stirring became a turbid emulsion. The micellar arrangement was confirmed by dynamic light scattering and optical microscopy. The new, green and metal free synthetic method enabled the execution of regiocontrolled tandem cycloaddition oxidation sequences leading to a library of pyrazole and isoxazoline derivatives.

Cobalt-catalyzed aerobic oxidative cyclization of β,γ- unsaturated oximes

Cobalt complex Co(nmp)2 can efficiently catalyze the aerobic oxidative 5-exo cyclization of β,γ-unsaturated oximes to afford isoxazolines. The key cyclization step involves the generation of carbon-centred radicals. The products are largely dep

A novel one-pot synthesis of hydroximoyl chlorides and 2-isoxazolines using N-tert-butyl-N-chlorocyanamide

Treatment of aldoximes with N-tert-butyl-N-chlorocyanamide gave hydroximoyl chlorides in quantitative yields in less than a minute, which on dehydrohalogenation in the presence of triethylamine gave the corresponding nitrile oxides. The nitrile oxides underwent 1,3-dipolar addition to dipolarophiles and gave 2-isoxazolines in excellent yields under mild conditions.

Synthesis of Isoxazolines and Isoxazoles via Generation of Nitrile Oxides from O-Stannyl Aldoximes

The reactions of O-tributylstannyl aldoximes and active halogen compounds such as tert-butyl hypochlorite or N-bromosuccinimide, whereby nitrile oxides are generated effectively, are applied to the preparations of isoxazolines and isoxazoles via d

SYNTHESIS OF ISOXAZOLINES AND ISOXAZOLES FROM ALDOXIMES BY THE USE OF SODIUM BROMITE WITH ORGANOTIN HALIDE

The oxidizing system using sodium bromite with a catalytic amount of tri-n-butyltin chloride is applied for the preparations of isoxazolines and isoxazoles from aldoximes via dipolar cycloaddition.

Reaction of Hydroximic Chlorides with Hexabutylditin. A Mild Method for Generation and Cycloaddition of Nitrile Oxides.

A new method for the in situ generation of nitrile oxides is reported.The reaction conditions are mild and neutral.

PHOTOCHEMISTRY OF 3-ARYL-2-ISOXAZOLINE

3-Phenyl-2-isoxazoline (1) was irradiated to give 4-phenyl-2-oxazoline (3), β-aminoaldehyde (14) and benzonitrile from its ?-?* singlet excited state.Several related derivatives afforded similar photoproducts on irradiation.The quantum yields of the photoreactions were dependent on the magnitudes of the singlet energies of the 2-isoxazolines. p-Cyanophenyl-2-isoxaline (1c) formed a one-to-one photoadduct (22) with benzene.