16089-66-0

Upstream product

• 57777-70-5 α,α-adamantylidene-N-methyl nitrone 
• 123-11-5 4-methoxy-benzaldehyde 
• 4229-44-1 N-methylhydroxyamine hydrochloride 
• 593-77-1 N-Methylhydroxylamine 
• 191991-30-7 N-p-methoxybenzyl-N-methylhydroxylamine 

Downstream Products

• 267238-10-8 trans-[PtCl₄(N=C(Me)O-N(Me)-C(H)(p-C₆H₄OMe))2] 
• 148368-43-8 2-methyl-3-p-methoxyphenyl-5,5-diphenylisoxazolidine 
• 102972-13-4 (3S*,3aS*,7S*,7aR*)-7-benzoyloxy-3-p-methoxyphenyl-2-methyl-4-oxo-tetrahydropyrano-<4,5-d>-isoxazolidine 
• 145616-54-2 Acetic acid 3-(4-methoxy-phenyl)-2-methyl-isoxazolidin-5-yl ester 
• 145616-44-0 2-methyl-3-p-methoxyphenyl-5-ethoxyisoxazolidine 
• 145616-44-0 2-methyl-3-p-methoxyphenyl-5-ethoxyisoxazolidine 
• 148345-16-8 4-ethoxycarbonyl-3-(4'-methoxyphenyl)-2-methyl-5-phenyl-4-isoxazoline 

Relevant academic research and scientific papers

(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route t

Crystal and molecular structure studies of (Z)-N-methyl-C-4-substituted phenyl nitrones by XRD, DFT, FTIR and NMR methods

(Z)-N-methyl-C-4-substituted phenyl nitrones –O+N(Me)=C(H)R (Z-2a R = 4-ClC6H4, Z-2b R = 4-NO2C6H4, Z-2c R = 4-CH3OC6H4) were synthesized and cha

1,3-Dipolar cycloaddition of nitrones to a nitrile functionality in closo -decaborate clusters: A novel reactivity mode for the borylated C≡N group

The Z-configured nitrones -O+N(Me)=C(H)C 6H4R2-p (R2 = OMe (2a), Me (2b), NO2 (2c)) react with the nitrile functionality of the closo-decaborate clusters [Bun4N][B10H 9(NCR1)] (R1 = Me (1a), Et (1b), But (1c), Ph (1d)) in CHCl3 solution under mild conditions (20-25 °C, 16-18 h) to afford the products of cycloaddition: viz., the borylated 2,3-dihydro-1,2,4-oxadiazoles [Bun4N][B10H 9{Na=CR1ON(Me)CbH(C 6H4R2-p)}](a-b) (3a-l). This reaction represents the first example of boron-mediated 1,3-dipolar cycloaddition of allyl anion type dipoles, i.e. nitrones, to the nitrile group. Alteration of the lipophilic [Bun4N]+ counterion with the hydrophilic Na+ via the metathetical reaction with NaBPh4 in 3a,b,e,f allows the modification of their hydrophilic-lipophilic properties and, consequently, solubility. Compounds 3a-j and 5a-d were characterized by high-resolution ESI-MS, IR, and 1H, 13C{1H}, and 11B{1H} NMR spectroscopy. The structures of 3a,e,f were determined by single-crystal X-ray diffraction.

1,3-Dipolar cycloadditions. Part XVII: Experimental and theoretical spectroscopic investigations of C-aryl-N-methyl nitrones

Detailed experimental and theoretical spectroscopic studies of C-aryl-N-methyl nitrones have been reported. The optimized geometries have been calculated by DFT/B3LYP level of theory with 6-31+G(d,p) basis set. The theoretically computed frontier orbital

Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines

Microwave irradiation allows increasing the speed of several reactions and also offers the possibility of eliminating poisoning organic solvents. In this work we report the microwave-assisted neat synthesis of α-phenyl-tert-butylnitrone (PBN) and other alkyl and aryl nitrones and also the rapid synthesis of isoxazolidines resulting from 1,3-dipolar cycloaddition of nitrones to ethyl trans-crotonate.

Synthesis of functionalized sulfonamides via 1,3-dipolar cycloaddition of pentafluorophenyl vinylsulfonate

(Matrix presented) An efficient intermolecular 1,3-dipolar cycloaddition of a variety of nitrones to pentafluorophenyl (PFP) vinylsulfonate is described. The transformation produces stable "reversed" cycloadducts of unprecedented stereo- and regioselectiv

Oxidation of N-benzyl-N-methylhydroxylamines to nitrones. A mechanistic study

Oxidation of various N-(o-, m-, p- substituted benzyl)- N-methylhydroxylamines has been carried out using mercury(II) oxide and p-benzoquinone (p-BQ) as oxidants. Hammett plots have been obtained with negative ρ values, showing the development of a positive centre in the transition state. The unstable E nitrones, which readily isomerize to the more stable Z nitrones, are obtained in appreciable quantities and in some cases as the major product. A considerable deuterium isotope effect is observed in the oxidation process. The overall picture of the mechanistic pathway involves electron transfer from nitrogen to the oxidant followed by hydrogen abstraction.

Chromium and Tungsten Pentacarbonyl Groups as Reactivity and Selectivity Auxiliaries in Cycloaddition of Alkynyl Fischer Carbene Complexes with N-Alkyl Nitrones

Alkynyl Fischer carbene complexes were found to undergo chemoselective, regioselective, and rate-enhanced 1,3-dipolar cycloaddition with nitrones to give 2,3-dihydroisoxazole carbene complexes in excellent yields.These alkynyl complexes can serve as synth

A Novel Nitrone Cycloaddition/ Rearrangement

Adamantanone-derived nitrone 4 and some other keto-nitrones, when reacted with aromatic and aliphatic aldehydes in refluxing toluene or tetrahydrofuran, formed the corresponding aldonitrones (Z)-10, the latter arising from the fragmentation of an initially formed 1,4,2-dioxazolidine 6 to adamantan-2-one and an oxaziridine intermediate 11, which then rearranges to (Z)-10.