58074-39-8

Upstream product

• 698-16-8 benzohydroximoyl chloride 
• 142-29-0 cyclopentene 
• 622-42-4 1-nitro-1-phenylmethane 
• 100-52-7 benzaldehyde 
• 932-90-1 Benzaldoxime 
• 62-53-3 aniline 
• 934-16-7 phenylhydroxamoyl chloride 
• 873-67-6 benzonitrile oxide 

Downstream Products

• 18721-49-8 2-phenyl-(3ar,6ac)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazole 
• 21573-70-6 (cyclopent-1-en-1-yl)(phenyl)methanone 
• 114589-97-8 1-hydroxy-2-benzoyl-cyclopentane 
• 114140-74-8 C₁₃H₁₆N₂O₃ 
• 32346-66-0 (2-hydroxy-cyclopentyl)-phenyl-methanone 
• 32346-66-0 (±)-2-hydroxycyclopentyl(phenyl)methanone 
• 69423-43-4 β-(1R,2R,1'R)/(1S,2S,1'S)-2-(α-Aminobenzyl)cyclopentanol 
• 100191-93-3 (E)-Cyclopentenylphenylketon-oxim 
• 34879-49-7 (Z)-Cyclopentenylphenylketon-oxim 

Relevant academic research and scientific papers

Kinetic solvent effects on 1,3-dipolar cycloadditions of benzonitrile oxide

The kinetics of 1,3-dipolar cycloadditions of benzonitrile oxide with a series of N-substituted maleimides and with cyclopentene are reported for water, a wide range of organic solvents and binary solvent mixtures. The results indicate the importance of both solvent polarity and specific hydrogen-bond interactions in governing the rates of the reactions. The aforementioned reactions are examples for which these factors often counteract, leading to a complex dependence of rate constants on the nature of the solvent. For the reactions of N-ethylmaleimide and N-n-butylmaleimide with benzonitrile oxide, isobaric activation parameters have been determined in several organic solvents, water, and water-1-propanol mixtures. Interestingly, the activation parameters reveal significant differences in solvation in different solvents that are not clearly reflected in the rate constants. In highly aqueous mixtures, enforced hydrophobic interactions lead to an increase in rate constant, relative to organic solvents. However, the overall rate enhancement in water is modest, if present at all, because the solvent polarity diminishes the rate constant. This pattern contrasts with common Diels-Alder reactions, where polarity, hydrogen-bond donor capacity and enforced hydrophobic interactions work together, which can result in impressive rate accelerations in water. Copyright

Aqueous phase preparation method of isoxazoline compound participating in vitamin E micro-micelle

The invention provides an aqueous phase synthesis method of the isoxazoline compound represented by the formula (III), wherein the benzaldehyde oxime represented by the formula (I) is a substrate, and the aqueous solution of the surfactant in the mass concentration 1 wt % - 5 wt % is N - chlorosuccinimide. Under the common action of the basic substance, the olefinic compound represented by the formula (II) is reacted 6 - 16h at room temperature, and the resulting reaction liquid is subjected to post-treatment to obtain the isoxazoline compound represented by the formula (III). Water serves as a reaction solvent, the use amount of the organic solvent is reduced, and zero emission of the solvent is realized.

Water-Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4-Oxadiazoles

Conventional methods generate nitrile oxides from oxime halides in organic solvents under basic conditions. However, the present work revealed that water-assisted generation of nitrile oxides proceeds under mild acidic conditions (pH 4-5). Cycloadditions of nitrile oxides with alkynes and alkenes easily occurred in water without using catalysts, thus yielding isoxazoles and isoxazolines, respectively, with excellent stereoselectivity toward five- and six-membered cyclic alkenes. A double stereoselective cycloaddition of two units of a nitrile oxide with cyclohexene was also achieved, thus yielding 1,2,4-oxadiazole derivatives having a unique hybrid isoxazoline-oxadiazole skeleton. Enantiomerically pure isoxazolines were prepared from monoterpenes with a ring strain. In one case, the isoxazoline with a butterfly-like structure was simply prepared, and it might be used as a ligand in asymmetric catalysis.

Copper-Catalyzed Oxidative Oxyamination/Diamination of Internal Alkenes of Unsaturated Oximes with Simple Amines

A convenient and versatile oxidative intra/intermolecular oxyamination and diamination of unactivated alkenes has been developed through copper-catalyzed radical reactions of β,γ- and γ,δ-unsaturated ketoximes with electron-rich aryl and aliphatic amines. These reactions were carried out by employing di-tert-butyl peroxide (DTBP) or air as the terminal oxidant, and a series of useful nitrogen-containing 4,5-dihydroisoxazoles and cyclic nitrones were formed.

1,3-Dipolar cycloadditions of benzonitrile oxide with various dipolarophiles in aqueous solutions. A kinetic study

The second-order rate constants for the 1,3-dipolar cycloaddition of benzonitrile oxide (1) with various dipolarophiles (2a-e) were determined in aqueous media and in organic solvents to gain more insight into the influence of an aqueous medium on pericyclic reactions. 1,3-Dipolar cycloadditions with electron-poor dipolarophiles are accelerated in water and protic solvents, whereas an aqueous medium has no special effect when electron-poor dipolarophiles are involved. These observations can be explained using frontier molecular orbital theory. In all cases, enforced hydrophobic interactions promote the reaction. These results are supported by kinetic experiments in waterethanol mixtures. Sodium dodecyl sulfate micelles accelerate the cycloaddition of 1 with both electron-rich and electron-poor dipolarophiles. More than for other systems, the present results show that hydrogen bonding and hydrophobic interactions can either cooperate or counteract each other in determining the kinetic medium effects in aqueous solutions.

Nitrosocarbonyl Intermediates as "Super-Enophiles": a Mild Method for Carbon-Nitrogen Bond Formation

Nitrosocarbonyl intermediates, generated at r.t. by the mild oxidation of nitrile oxides, undergo clean ene reactions with tetramethyl- and trimethyl-ethylene and with cyclohexene.With less substituted ethylenes the ene pathway is still active but the oxidation step of the nitrile oxides competes with the cycloadditions to the olefins. - Keywords: Cycloadditions; Ene reactions; Nitrile oxides; Nitroso compounds

An improved synthesis of isoxazolines based on Tprssell's procedure

Isoxazolines (1-29) have been prepared in 65-75percent yield by cycloaddition of alkenes to benzonitrile oxide, 4-chlorobenzonitrile oxide and 3-nitrobenzonitrile oxide generated in situ from the respective araldoximes.A number of new isoxazolines such as

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.

Synthesis via Isoxazolines, 4. - Base-initiated Ring Opening of 2-Isoxazolines; Synthesis of α-Enoximes and -Enones from Alkenes

The 2-Isoxazolines 2a-e and 5 undergo ring cleavage on treatment with lithium diisopropylamide (LDA) at -78 --> 0 deg C to afford sterically homogeneous α-enoximes 3a-e and 6. 1H- and 13C-NMR data establish that these compounds have retained the C=N-configuration of the starting isoxazoline.Subsequent deoximation by acidic TiCl3 solution in DMF yields the α-enones 4a-e and the tetrahydropyran 7, respectively.This constitutes a new, regioselective sequence (1 --> 4) for the acylation of alkenes, which avoids cationic intermediates.Studies to determine the mechanistic course and the scope of the ring cleavage reaction show that endo and/or exo anions are formed first, depending on the substitution pattern.The former may isomerize ( -78 deg C) to produce enoximates; both offer the possibility to prepare new 4- or 3α-substituted isoxazolines by the reaction with electrophiles as demonstrated by two examples (2f, 2h).