92506-32-6

Upstream product

• 3717-22-4 (Z)-para-methoxybenzaldehyde oxime 
• 100-44-7 benzyl chloride 
• 872848-25-4 [3-(4-methoxy-phenyl)-oxaziridin-2-yl]-acetic acid methyl ester 
• 622-33-3 N-benzyloxyamine 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 872984-87-7 (S)-2-[3-(4-Methoxy-phenyl)-oxaziridin-2-yl]-propionic acid methyl ester 
• 872984-86-6 (S)-2-[3-(4-Methoxy-phenyl)-oxaziridin-2-yl]-3-methyl-butyric acid methyl ester 
• 73995-68-3 (S)-2-[3-(4-Methoxy-phenyl)-oxaziridin-2-yl]-4-methyl-pentanoic acid methyl ester 
• 73995-67-2 (S)-2-[3-(4-Methoxy-phenyl)-oxaziridin-2-yl]-3-phenyl-propionic acid methyl ester 
• 126079-16-1 methyl N-(4-methoxybenzylidene)glycinate 
• 123-11-5 4-methoxy-benzaldehyde 
• 3717-21-3 p-methoxyl benzaldoxime 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 140451-68-9 2-[3-[(Z)-Benzyloxyimino]-3-(4-methoxy-phenyl)-2-oxo-propyl]-isoindole-1,3-dione 

Relevant academic research and scientific papers

Metal-Free Transformation of Sulfonyl Oxime Ethers with Amines to Oxime Ethers

Sulfonyl oxime ethers undergo facile radical substitutions with various amines to yield the corresponding oxime ethers. An efficient arylation of sulfonyl oxime ethers was accomplished under ambient temperature and metal-free conditions, with a wide range of functional group tolerance. Mechanistic investigations indicate that a phenyl radical is involved in the catalytic cycle.

Sustainable Synthesis of Oximes, Hydrazones, and Thiosemicarbazones under Mild Organocatalyzed Reaction Conditions

Pyrrolidine catalyzes very efficiently, presumably via iminium activation, the formation of acyloximes, acylhydrazones, and thiosemicarbazones derived from aromatic and aliphatic aldehydes using equimolar amounts of reagents and green solvents. Experimental simplicity and excellent yields after a simple filtration are the main advantages of the method, being an alternative to those currently available especially for the acyl derivatives, which do not work under uncatalyzed conditions. Its application to the synthesis of acyloximes by direct condensation between aldehydes and acylhydroxylamines is unprecedented.

Metal-Free 2,2,6,6-tetramethylpiperidin-1-yloxy radical (TEMPO) catalyzed aerobic oxidation of hydroxylamines and alkoxyamines to oximes and oxime ethers

TEMPO-Mediated oxidation of hydroxylamines (=hydroxyamines) and alkoxyamines to the corresponding oxime derivatives is reported (TEMPO=2,2,6,6-tetramethylpiperidin-1-yloxy radical; Scheme 2). These environmentally benign oxidations proceed in good to excellent yields (Table 1). For alkoxyamines, oxidation to the corresponding oxime ethers can be performed by using dioxygen as a terminal oxidant in the presence of 5-10 mol-% of TEMPO or 4-substituted derivatives thereof as a catalyst (Scheme 3 and Table 2). Importantly, benzyl bromides can directly be transformed to oxime ethers via in situ alkoxyamine formation by a nucleophilic substitution followed by TEMPO-mediated oxidation (Scheme 4 and Table 3). Copyright

Optically pure N-hydroxy-O-triisopropylsilyl-α-L-amino acid methyl esters from AlCl3-assisted ring opening of chiral oxaziridines by nitrogen containing nucleophiles

This article reports a straightforward and unprecedented process of AlCl3-assisted oxaziridine ring opening by nitrogen containing nucleophiles, in a totally anhydrous milieu. Under these conditions, nucleophiles exclusively attack the carbon atom of the three-membered heterocycles, obtained from methyl esters of natural α-amino acids, generating N-hydroxy-α-L-amino acid methyl esters. No nitrones, amides, or other side products, either from unwanted rearrangements or due to the attack of the nucleophile on the N atom of the oxaziridine systems, are formed. The hydroxylamine compounds are recovered in excellent yields, after their site-specific conversion into the corresponding O-triisopropylsilyl derivatives, by exposure to triisopropylsilyl triflate in the presence of 1H-imidazole. Derivatization, performed immediately after the recovery of the N-hydroxylated precursors, allows the chiral integrity of the asymmetric α-carbon atoms in the amino acid methyl esters to be retained. It also protects the obtained compounds from frame degradation by disproportionation. N-Hydroxy-O- triisopropylsilyl-α-L-amino acid methyl esters are important intermediates in the study of natural α-L-amino acid metabolic pathways and are ideal candidates as starting materials in the synthesis of biologically, pharmacologically, and nutritionally important N-hydroxy peptides.

Tandem oxidation processes: The direct conversion of activated alcohols into oximes; synthesis of citaldoxime

The direct conversion of primary alcohols into oximes is reported using manganese dioxide and alkoxylamines/hydroxylamine as their hydrochloride salts or supported on Amberlyst 15. This transformation has been applied to a range of benzylic, allylic and propargylic alcohols and utilised to prepare the natural product citaldoxime.

N-nitroso-N,O-dialkylhydroxylamines: Preparation, structure, and mechanism of the hydronium ion catalysed solvolytic nitrous oxide extrusion reaction

Eleven N-nitroso-N,O-dialkylhydroxylamines, RN(NO)OR′, have been prepared and the mechanisms of their hydronium ion catalysed solvolyses in aqueous solution which liberate nitrous oxide have been investigated. All reactions are first-order in substrate and first-order in hydronium ion, and the second-order rate constants at 25°C vary over a range of less than 140 in spite of considerable variation in substrate structure (R ranges from methyl to 4-methoxybenzyl to 2-adamantyl, for example) and changes in solvent composition (water with up to 50% methanol or 66% acetonitrile). Enthalpies and entropies of activation are qualitatively similar throughout the range (ΔH?= 72-93 kJ mol-1 and ΔS? = -19 to -57 J K-1 mol-1) which, with the product analyses, are accommodated by a mechanism involving pre-equilibrium protonation of the substrates followed by rate-limiting dissociation to give RN2O+ and HOR′. The oxodiazonium ion intermediate, RN2O+, then dissociates further to give the carbenium ion intermediate, R+, or suffers direct nucleophilic displacement of N2O by solvent (the external nucleophile) or by R′OH (the internal nucleophile liberated in the initial fragmentation). The carbenium ion, R+ (if formed), suffers nucleophilic capture either by solvent or by R′OH. When acetonitrile is the co-solvent (rather than methanol) for the N-(2-adamantyl) substrate 3g, the product of the Ritter reaction, 2-acetamidoadamantane, is detected. These nitrous oxide liberating reactions are compared with the nitric oxide liberating reactions of related N-nitrosohydroxylamines, and the origin of the difference between them is identified. The N(1)-nitroso group in the N,O-dibenzyl compound 3c is shown by X-ray crystallography to be essentially coplanar with the C and O atoms also bonded to N(1).

Alkylative amination of aldehydes via carbon-carbon bond formation based on radical addition to carbon-nitrogen double bond

Alkylative amination of aldehydes was achieved via a carbon-carbon bond formation by the intermolecular alkyl radical addition to the carbon-nitrogen double bond of oxime ethers generated in situ from aldehydes and benzyloxyamine. Alkyl radical addition t

C-ACYLATION OF AZOMETHINE GROUP IN O-BENZYL AROMATIC ALDOXIMES

Reaction of four O-benzyl aromatic aldoximes with phthalimidoacetyl chloride, 3,5-dinitrobenzoyl chloride or phthalimidoacetic-p-toluenesulfonyl anhydride in the presence of triethylamine afforded moderate yields of C-acylation products of the azomethine group.Mechanism of the reaction is discussed.