Reaction Of N-oxide Research Articles

The reaction of heteroaromatic N-oxide with acid chloride and cyanide. IX. On p-tolylsulfonylation on side-chain carbon in 2-methylquinoline 1-oxide and related compounds (author's transl)

The reaction of heteroaromatic N-oxide with acid chloride and cyanide. IX. On p-tolylsulfonylation on side-chain carbon in 2-methylquinoline 1-oxide and related compounds (author's transl)

The reaction of heteroaromatic N-oxide with acid chloride and cyanide. VIII. On the reaction of phenanthridine 5-oxide or acridine 10-oxide with sulfonic acid chloride and potassium cyanide (author's transl)

The reaction of heteroaromatic N-oxide with acid chloride and cyanide. VIII. On the reaction of phenanthridine 5-oxide or acridine 10-oxide with sulfonic acid chloride and potassium cyanide (author's transl)

The reaction of heteroaromatic N-oxide with acid chloride and cyanide. VII. On the reaction of pyridine 1-oxides with sulfonic acid chloride and potassium cyanide (author's transl)

The reaction of heteroaromatic N-oxide with acid chloride and cyanide. VII. On the reaction of pyridine 1-oxides with sulfonic acid chloride and potassium cyanide (author's transl)

The reaction of heteroaromatic N-oxide with acid chloride and cyanide. IV. On the reaction of 2,4-disubstituted quinoline 1-oxides with sulfonic acid chloride and potassium cyanide (author's transl)

The reaction of heteroaromatic N-oxide with acid chloride and cyanide. IV. On the reaction of 2,4-disubstituted quinoline 1-oxides with sulfonic acid chloride and potassium cyanide (author's transl)

A new synthesis of dihydromancunine.

Dihydromancunine, a model for a proposed indole alkaloid biosynthetic intermediate, mancunine, was synthesized using a modified Polonovski reaction of desmethylhirsutine N-oxide, which was derived from the indole alkaloid hirsutine.

The reaction of heteroaromatic N-oxide with acid chloride and cyanide. VI. On the reaction of isoquinoline 2-oxides with sulfonic acid chloride and potassium cyanide (author's transl)

The reaction of heteroaromatic N-oxide with acid chloride and cyanide. VI. On the reaction of isoquinoline 2-oxides with sulfonic acid chloride and potassium cyanide (author's transl)

ChemInform Abstract: REACTION OF AROMATIC N‐OXIDES WITH DIPOLAROPHILES. II. REACTION OF β‐ALKYLPYRIDINE N‐OXIDES WITH PHENYL ISOCYANATE

AbstractDie Reaktion der Pyridin‐N‐oxide (I) mit Phenylisocyanat (II) wird untersucht und liefert Mischungen aus den isomeren Cycloaddukten (III) und (IV) sowie den isomeren Aminen (V) und (VI), die zum Teil aus ersteren bei der Behandlung mit Alkali gebildet werden können.

Reaction of benzofurazan N-oxide with secondary aliphatic amines; preparation of NN-dialkyl-N′-(o-nitrophenyl)hydrazines

The interaction of benzofurazan N-oxide with a variety of secondary aliphatic amines in the cold gives NN-dialkyl-N′-(o-nitrophenyl)hydrazines by attack on the hetero-ring. At higher temperatures, dialkylaminobenzofurazans are obtained by attack on the benzene ring. Substituents in the benzofuran N-oxide exerting –I and –M effects slow down both processes. The interaction of various NN-dialkylhydrazines with chloronitrobenzenes and polynitrobenzenes give either nitrophenyldialkyl-amines or -hydrazines in a predictable manner, for which a mechanistic rationale is proposed, involving charge-transfer complex formation when polynitrobenzenes are used.

Reaction of aromatic N-oxides with dipolarophiles. II. Reaction of .BETA.-alkypyridine N-oxides with phenyl isocyanate.

The reaction of β-alkylpyridine N-oxides (I) with phenyl isocyanate (II) in dimethyl-formamide at 110° gave the cycloadducts (III and IV), although it was noticed that the reaction of pyridine N-oxide with II directly affords α-anilinopyridine. The duration at elevated temperature resulted in an increased yield of the anilino derivatives, while the cycloadducts tended to decrease. The effect by using various sorts of solvents demonstrated that dimethylformamide and dimethylsulfoxide are suitable for the formation of cycloadducts.

Deuterium isotope effects and the influence of solvent in the redox and rearrangement reactions of 2-picoline N-oxide and phenylacetic anhydride

The reaction of 2-picoline N-oxide with phenylacetic anhydride proceeds by two paths: rearrangement to produce picolyl phenylacetate, 2-(β- phenylethyl)pyridine, other minor rearrangement products, and CO2, and oxidation to give benzaldehyde, 2-picoline, and CO2. The ratio of the competing processes is sensitive to the incorporation of deuterium at appropriate sites in the reactants, thereby permitting a convenient method for determining hydrogen isotope effects. For rearrangement, a primary kinetic isotope effect value (3.8 to 4.2) is obtained when reactions of methyl-deuterated and undeuterated 2-picoline N-oxide are compared, confirming earlier work on related systems that anhydro base formation is rate determining. Oxidation, however, manifests an inverse isotope effect (0.76 to 0.81, deuterium labeling at the methylene groups of phenylacetic anhydride) which, along with other evidence, suggests reversible enol or enolate formation prior to an SN1'-like rate- determining step to generate the reactive carbocation or its conjugate base. Solvent polarity also significantly, but not dramatically, affects the ratio of the competing pathways. A trend is established which supports the proposed mechanisms if they are modified to include ion pairing phenomena. Furthermore, the influence of solvent polarity was found to be consistent with a dual mode of fragmentation of the anhydro base intermediate.

Evidence for an Ionic Mechanism for the Reaction of 2-Cyclopropylpyridine N-Oxide with Acetic Anhydride.

Evidence for an Ionic Mechanism for the Reaction of 2-Cyclopropylpyridine N-Oxide with Acetic Anhydride.

Studies on the Reactivity of Isoquinoline and Related Compounds. I. Reaction of Isoquinoline N-Oxide with Diketene

Studies on the Reactivity of Isoquinoline and Related Compounds. I. Reaction of Isoquinoline N-Oxide with Diketene

Studies on pyridazines. XXIV. The reaction of pyridazine N-oxides and pyridazinium ylides with benzyne.

The reaction of pyridazine N-oxide (1) with benzyne produced 1-benzoxepine (5) in moderate yield, via the 1, 3-cycloadduct (4). By the similar reaction, N-acetyliminopyridazinium ylide (2) and pyridazinium dicyanomethylide (3) yielded the 1, 3-cycloadducts (9 and 21). The adduct (9) was transformed into the 3-vinylindazole (10) and 3-(2-acetoanilino)-pyridazine (11) by heating or treatment with sodium methoxide. Irradiation of the adduct (9) resulted in the aromatization to form indazolo[2, 3-b]pyridazine (12) and in the ring contraction to form indole derivatives (13 and 14) via 1-benzazepine (19). The formation mechanism of these compounds is also discussed.

Reaction of pentachloropyridine N-oxide with potassium hydrogen sulfide

Depending on the conditions, the reaction of pentachloropyridine N-oxide with potassium hydrogen sulfide leads to the N-oxide of the potassium salt of 3,4,5,6-tetrachloropyridin-2-thiol or the dipotassium salt of 3,4,5-trichloropyridine-2,6-dithiol, which are converted by the action of dimethyl sulfate into the corresponding methylthio derivatives. Oxidation of the latter has given sulfones. It has been shown that for these sulfones,reactions with nucleophilic reagents take place at the methylsulfonyl group and not at the chlorine atoms.

Studies on tertiary amine oxides. XLVI. The reaction of quinoline N-oxide with sodium nitrite in the presence of tosyl chloride (author's transl)

Studies on tertiary amine oxides. XLVI. The reaction of quinoline N-oxide with sodium nitrite in the presence of tosyl chloride (author's transl)

Studies on tertiary amine oxides. XLVIII. The reaction of quinoline N-oxide with acrylonitrile.

Studies on tertiary amine oxides. XLVIII. The reaction of quinoline N-oxide with acrylonitrile.

Reaction of 4-Picoline N-Oxide with Acetic Anhydride as Studied by Chemically Induced Dynamic 13C Polarization (CIDNP)

Abstract The 13C spectrum taken during the reaction of 4-picoline N-oxide with acetic anhydride at 110 °C in the NMR cavity (23.5 kG) shows a pair of emission lines at 15.8 and 154.4 ppm and enhanced absorption at 29.6 and 125.0 ppm (TMS-based). The signals are found to be due to 4-ethylpyridine formed as a minor product of the reaction and are interpreted in terms of the memory effect of the polarization induced in the precursor 4-picolyl-acetoxy radical pair.

Reaction of pyridine N-oxide with acetic anhydride in anisole and in benzonitrile

Reaction of pyridine N-oxide with acetic anhydride in anisole and in benzonitrile

Reactions of Amine Oxides and Hydroxylamines with Sulfur Dioxide

Strychnine N-oxide (8; X = H) reacts with sulfur dioxide in benzene to form the sulfitoamine 9 (X = H), which rearranges in boiling water to the substituted sulfamic acid 10 (X = H) by a free-radical mechanism. The sulfamic acid 10 (X = H) is also formed by reaction of strychnine N-oxide with cold aqueous sulfur dioxide, and may be an intermediate in the reduction of the amine oxide by sulfur dioxide in hot water. With aqueous sulfur dioxide at 0°, N,N-dimethylbenzylamine N-oxide gives tertiary amine by reduction and secondary amine and aldehyde by a Polonovski-type reaction; however, N,N-dimethylaniline N-oxide gives tertiary amine, o- and p-dimethylaminobenzene sulfonic acids, but no appreciable amount of secondary amine. The sulfonic acids are probably formed by a free-radical mechanism, since their formation is largely suppressed by the addition of hydroquinone. The reactions of hydroxylamine and of β-phenylhydroxylamine with sulfur dioxide in water have also been studied.

Kinetics of the exchange reaction of 3-picoline N-oxide with hexakis(3-picoline N-oxide)nickel(II)

Kinetics of the exchange reaction of 3-picoline N-oxide with hexakis(3-picoline N-oxide)nickel(II)