34879-53-3

Upstream product

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

Downstream Products

• 34879-49-7 (Z)-Cyclopentenylphenylketon-oxim 
• 100191-93-3 (E)-Cyclopentenylphenylketon-oxim 
• 69423-43-4 β-(1R,2R,1'R)/(1S,2S,1'S)-2-(α-Aminobenzyl)cyclopentanol 
• 21573-70-6 (cyclopent-1-en-1-yl)(phenyl)methanone 
• 32346-66-0 (±)-2-hydroxycyclopentyl(phenyl)methanone 
• 32346-66-0 (2-hydroxy-cyclopentyl)-phenyl-methanone 

Relevant academic research and scientific papers

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.

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

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).