917-95-3

Usage

InChI:InChI=1/C4H9NO/c1-4(2,3)5-6/h1-3H3

Upstream product

• 527-69-5 2-furancarbonyl chloride 
• 2406-25-9 di-tert-butyl nitroxide 
• 336-64-1 bis(heptafluorobutyryl) peroxide 
• 75-09-2 dichloromethane 
• 67-66-3 chloroform 
• 3376-24-7 N-tert-butyl-α-phenylnitrone 
• 118891-54-6 methyl N-(1,1-dimethylethyl)benzenecarboximidate N-oxide 
• 874-60-2 4-methyl-benzoyl chloride 
• 122-01-0 4-chloro-benzoyl chloride 
• 933-88-0 ortho-toluoyl chloride 
• 3376-24-7 (Z)-N-benzylidene-2-methylpropan-2-amine oxide 
• 75-64-9 tert-butylamine 
• 6852-58-0 N-benzylidene tert-butylamine 
• 594-70-7 2-Methyl-2-nitropropane 

Downstream Products

• 58796-22-8 N-t-Butyl-α-phenyl-α-methylnitron 
• 53104-17-9 N-tert-Butyl-N-pentafluorophenyl-hydroxylamine 
• 53104-09-9 N-tert-Butyl-N-(3-fluoro-phenyl)-hydroxylamine 
• 53104-10-2 N-tert-Butyl-N-(5-fluoro-2-methyl-phenyl)-hydroxylamine 
• 65754-13-4 tert-Butyl-2-methyl-5-trifluorphenylhydroxylamin 
• 53104-01-1 N-tert-Butyl-N-(4-methylsulfanyl-phenyl)-hydroxylamine 
• 53104-19-1 N-tert-Butyl-N-(2,3,5,6-tetrafluoro-phenyl)-hydroxylamine 
• 53104-18-0 N-tert-Butyl-N-(2,3,4,6-tetrafluoro-phenyl)-hydroxylamine 
• 53104-07-7 N-tert-Butyl-N-(3-propyl-phenyl)-hydroxylamine 
• 53104-20-4 t-Butyl-2.3.4-trimethoxyphenylhydroxylamin 
• 53104-00-0 N-tert-Butyl-N-(3-methylsulfanyl-phenyl)-hydroxylamine 
• 53104-13-5 N-tert-Butyl-N-(3-dimethylamino-phenyl)-hydroxylamine 
• 65754-18-9 3,5-Di-t-butylphenyl-t-butylhydroxylamin 
• 53104-11-3 N-tert-Butyl-N-(4-dimethylamino-phenyl)-hydroxylamine 

Relevant academic research and scientific papers

Nitrone Directing Groups in Rhodium(III)-Catalyzed C?H Activation of Arenes: 1,3-Dipoles versus Traceless Directing Groups

Functionalizable directing groups (DGs) are highly desirable in C?H activation chemistry. The nitrone DGs are explored in rhodium(III)-catalyzed C?H activation of arenes and couplings with cyclopropenones. N-tert-butyl nitrones bearing a small ortho subst

Six-coordinate ferric porphyrins containing bidentate N-t-butyl-N-nitrosohydroxylaminato ligands: Structure, magnetism, IR spectroelectrochemisty, and reactivity

NONOates (diazeniumdiolates) containing the [X{N2O2}]- functional group are frequently employed as nitric oxide (NO) donors in biology, and some NONOates have been shown to bind to metalloenzymes. We report the preparation, crystal structures, detailed magnetic behavior, redox properties, and reactivities of the first isolable alkyl C-NONOate complexes of heme models, namely (OEP)Fe(η2-ON(t-Bu)NO) (1) and (TPP)Fe(η2-ON(t-Bu)NO) (2) (OEP = octaethylporphyrinato dianion, TPP = tetraphenylporphyrinato dianion). The compounds display the unusual NONOate O,O-bidentate binding mode for porphyrins, resulting in significant apical Fe displacements (+0.60 ? for 1, and +0.69 ? for 2) towards the axial ligands. Magnetic susceptibility and magnetization measurements made from 1.8-300 K at magnetic fields from 0.02 to 5 T, yielded magnetic moments of 5.976 and 5.974 Bohr magnetons for 1 and 2, respectively, clearly identifying them as high-spin (S = 5/2) ferric compounds. Variable-frequency (9.4 GHz and 34.5 GHz) EPR measurements, coupled with computer simulations, confirmed the magnetization results and yielded more precise values for the spin Hamiltonian parameters: gavg = 2.00 ± 0.03, D = 3.89 ± 0.09 cm-1, and E/D = 0.07 ± 0.01 for both compounds, where D and E are the axial and rhombic zero-field splittings. IR spectroelectrochemistry studies reveal that the first oxidations of these compounds occur at the porphyrin macrocycles and not at the Fe-NONOate moieties. Reactions of 1 and 2 with a histidine mimic (1-methylimidazole) generate RNO and NO, both of which may bind to the metal center if sterics allow, as shown by a comparative study with the Cupferron complex (T(p-OMe)PP)Fe(η2-ON(Ph)NO). Protonation of 1 and 2 yields N2O as a gaseous product, presumably from the initial generation of HNO that dimerizes to the observed N2O product.

Spin adducts from the reaction between N-phenyl-α-tert-butylnitrone (PBN) and activated olefins. A facile pathway converting PBN into 2-methyl-2-nitrosopropane (MNP)

N-Phenyl-α-tert-butylnitrone (PBN) reacts with activated olefins RCH=CHR, such as maleimides, maleic anhydride or diethyl maleate, with formation of two types of persistent spin adducts giving characteristic EPR spectra, denoted types A and B. Spin adducts with type A spectrum were formed photochemically and identified as reductive coupling products between the olefin and PBN, RCH2CH(R)-PBN.. Spin adducts with type B spectra were formed photochemically and/or thermally and were identified as reductive coupling products RCH2CH(R)-N(O.)But between the olefin and a degradation product of PBN, 2-methyl-2-nitrosopropane (MNP, t-BuNO). The conversion of PBN to t-BuNO was studied for a compound with an exceedingly reactive nitrogen-nitrogen double-bond, namely 4-phenyl-4H-1,2,4-triazoline-3,5-dione (PTAD). In this case, a 74% yield of t-BuNO was obtained in a short period of time; α,N-diphenylnitrone reacted similarly to give nitrosobenzene. The reaction between PBN and an activated olefin was assumed to occur analogously, either via the initial formation of a 1,3-dipolar cycloadduct or some parallel reaction involving attack of the electrophilic olefin at the PBN α-carbon. The 1,3-dipolar cycloadduct between PBN and N-phenylmaleimide exhibited favourable initiator properties for living polymerization of styrene. A new type of spin adduct, RCH(But)CH(R)-N(O.)But, was prepared by the photochemical reaction between an activated olefin and t-BuNO. This reaction presumably proceeds by photocleavage of t-BuNO to NO and t-Bu., the latter reacting with the activated olefin to give a transient radical, RCH(But)CH.(R), which is trapped by t-BuNO. Acta Chemica Scandinavica 1998.

Organo Sulfonic Peracids. 4.1 the Reaction of Arenesulfonylimidazoles with H2O2 in the Presence of Ketones. A New Entry to Dioxiranes

The reaction of ketones (acetone, 1,1,1-trifluoropropan-2-one) with the oxidation system (arene-sulfonyl)imidazole (2)/H2O2/NaOH permits the in situ generation of the corresponding dimethyl-and methyl(trifluoromethyl)dioxirane in various solvents. This has been established by the chemoselective oxidation of azomethines 6, the diastereoselective oxidation of cholesterol (12), and 18O-labeling experiments. Because only 5 equiv of ketone are used, the dioxirane oxidation pathway appears to be virtually exclusive one in this system. One example for the nonaqueous in situ generation of dimethyldioxirane (1a) is given.

Action d'un Tetrafluoroborate d'Oxaziridinium sur les Amines et les Imines

The Oxaziridinium salt 1 derived from dihydroisoquinolin is an oxygen transfer reagent to primary amines leading to nitrosoderivatives (if R = Alkyl) or nitro compounds (if R = Aryl), to tertiary amines leading to N-oxides, and to secondary amines and imines leading to the corresponding nitrone.

Reactions of Tris(trimethylsilyl)silyl Radicals with Nitroalkanes. EPR, Kinetic, and Product Studies

The radical-initiated reaction of tris(trimethylsilyl)silane with a variety of aliphatic nitro derivatives has been investigated.This silane, which for many applications is a valid alternative to tributyltin hydride, is unable to reduce tertiary nitroalkanes to the corresponding hydrocarbons.EPR results, as well as kinetic and products studies, have shown that this "anomalous" behavior is due to the fact that the nitroxide adducts formed by addition of tris(trimethylsilyl)silyl radicals to the nitro compounds fragment preferentially at the nitrogen-oxygen bond ratherthan at the carbon-nitrogen bond as in the analogous tributyltin adducts.The resulting silyloxy radical, (Me3Si)3SiO, undergoes a fast rearrangement (k 107 s-1 at room temperature) with migration of a Me3Si group from silicon to oxygen to give (Me3Si)2SiOSiMe3 which adds to the nitro compound affording a secondary nitroxide adduct.The kinetics of the decay of both primary and secondary adducts to nitromethane has been studied over a wide range of temperatures.With tertiary nitroalkanes persistent aminyl radicals, RNOSi(SiMe3)3, have also been detected.

α-Heteroatom-Substituted Nitrones. Synthesis and Reactions of Acyclic α-Alkoxynitrones

A general method was developed for the synthesis of acyclic α-alkoxynitrones (imidate N-oxides), a relatively new class of compounds.Regioselective alkylation of hydroxamic acids under neutral conditions with alkyl trifluoromethanesulfonates (triflates) gave nitrone hydrotriflates, and deprotonation by one of three methods gave the rather unstable nitrones in overall yields from 4 to 85percent.A wide range of substitution was possible, with R = H, Me, or Ar, R1 = Me or t-Bu, and R2 = Me or Et.The reactivity of these nitrones toward examples of various classes of reagents was investigated.Nitrone 3e (R = H, R1 = t-Bu, R2 = Me), the most reactive one studied, gave the following results: (1) with nucleophiles (aniline, n-butylamine, thiophenol, n-butyl mercaptan, and potassium cyanide), substitution of the α-OMe group produced new nitrones with amino, thio, and cyano groups in the α position; (2) with a reducing agent (NaBH4), N-tert-butylnitrone was formed; (3) with an oxidizing agent (m-chloroperbenzoic acid), oxidation and cleavage gave methyl formate and 2-methyl-2-nitrosopropane monomer and dimer; (4) with an electrophilic acylating agent (p-nitrobenzoyl chloride), methyl p-nitrobenzoate, N,O-bis(p-nitrobenzoyl)-N-tert-butylhydroxylamine, and N-tert-butyl-O-(p-nitrobenzoyl)hydroxylamine were produced.In parallel with the similar reactivity of aldo- and ketonitrones to ketones, the present α-alkoxynitrones undergo reactions analogous to those of esters with nucleophilic-type reagents.

Oxidation of Amines with 2-Sulfonyloxaziridines (Davis' Reagents)

2-(Phenylsulfonyl)-3-aryloxaziridines (Davis' Reagents) react rapidly with amines that are more basic than pyridine to give products that are dependent upon the structure of the amine.Tertiary aliphatic amines are oxidized to the corresponding N-oxides in high yields, while secondary aliphatic amines give the N,N-disubstituted hydroxylamines and corresponding nitrones in variable, stoichiometrically dependent ratios.Primary aliphatic amines give 10-35percent yields of nitroso compounds and 50-65percent yields of N-arylideneamines formed by the transimination reaction of the amine with the N-arylidenebenzenesulfonamide generated following oxygen transfer from the 2-(phenylsulfonyl)-3-aryloxaziridine.

An electron spin resonance spin trapping investigation of azide oxidation on TiO2 powder suspensions

The oxidation of azide has been studied on TiO2 powder suspensions in water, methanol, and mixtures of the two solvents.The esr spin trapping technique has been employed to provide evidence for the formation of azidyl radicals N.3.The results show that an aqueous alkaline medium is necessary to obtain a high production of N.3 radicals.A mechanism is proposed whereby the oxidation of N-3 is mainly due to reaction with OH. radicals which are in turn generated upon capture of holes by OH- groups adsorbed on TiO2.Azidyl anions adsorb weakly on TiO2 and do not displace adsorbed OH- from the surface.

Homosolvolysis. Part 3. The Reaction of Aromatic Acid Chlorides with Di-t-butyl Nitroxide

N-Aroyl-O-aroyl-N-t-butylhydroxylamines are formed when aromatic acid chlorides react with di-t-butyl nitroxide.