Reaction of haloazoxybenzenes with sulfuric acid.

スポンサーリンク

概要

• 論文の詳細を見る

• Treatment of 4,4′-dihaloazoxybenzenes with sulfuric acid afforded 4,4′-dihaloazobenzenes (<B>6</B>) as the major product and 5-halo-2-(<I>p</I>-halophenylazo)phenols, the Wallach rearrangement products as minor products, besides 2-halo-5-(<I>p</I>-halophenylazo)phenols, 2-halo-4-(<I>p</I>-halophenylazo)phenols, and 4-(<I>p</I>-halophenylazo)phenols as abnormal rearrangement products. The reaction of fluoro compound gave the azophenols (<B>3a</B> or <B>5a</B>) in the best yields. However, the ratio of <B>3a</B> to <B>5a</B> was found to vary with the concentration of sulfuric acid. Treatment of 4-haloazoxybenzenes with sulfuric acid gave 4-(<I>p</I>-halophenylazo)phenols and 4-haloazobenzenes (<B>13</B>) as major products together with 2-(<I>p</I>-halophenylazo)phenols and 5-halo-2-(phenylazo)phenols as minor products. Yields of reduction products <B>6</B> and <B>13</B> increased as the halosubstituent became heavier in the following sequence: F→Cl→Br→I.

• 公益社団法人 日本化学会の論文

著者

• Fujimori Ken

  Department Of Anatomy School Of Medicine Faculty Of Pharmaceutical Sciences Tokushima University

• Shimao Ichiro

  Department Of Applied Chemistry. Faculty Of Engineering Toyama University

• Oae Shigeru

  Deparment of Applied Chemistry Faculty of Engineering Osaka City University

• Fujimori Ken

  Department of Chemistry, The University of Tsukuba

関連論文

• A Thermolytic Azulene Synthesis from Dimethyl 4-Morpholino-3,3a,8,8a-tetrahydroazulene-5,6-dicarboxylates and Its 1-Substituted Derivatives
• Synthesis and Properties of Azuleno[1,2-a]acenaphthylene and Dimethyl acenaphthyleno[1,2-d]heptalene-8,9-dicarboxylate
• "Highly Destabilized Carbocations," Generation and Rearrangements in the Reactino of 8,9,10,11-Tetrahydrocyclohepta[a]phenalen-6(12H)-one-12-ol and -7(12H)-one-12-ol with Sulfuric Acid
• Triplet Sensitized Laser Flash Photolysis of BNN3, Caged Nitric Oxide
• Design and Synthesis of Dioxetane-Based Chemiluminescent Substrates with High Efficiency in Aqueous System(By a grant Research Institute for Integrated Science, Kanagawa University)
• Mechanistic Aspects of Bioluminescence and Chemiluminescence(By a grant Reserch Institute for Integrated Science, Kanagawa University)
• Studies on Heterogeneity of Fluorescence Labeled Chromatin
• Display on Dehydrogenase Distribution in Tissues by the TRIDENT
• CATCH22 syndrome with qastroesophageal reflux
• Reaction Kinetics of Nitroblue tetrazolium (NBT) Reduction
• Comparative studies on fish tooth tissues by microfluorometry and Raman-spectrometry
• UV-spectrophotometry and fluorophotometry on human tooth tissues
• MULTIPLE DISTRIBUTION OF THE FLUORESCENCE IN HUMAN TEETH (Symposium on the Chinical Application of Histochemistry and Cytochemistry)
• NONLYSOSOMAL GRANULES IN PERITONEAL MACROPHAGES : SUBCELLULAR LOCALIZATION OF NEUTRAL α-GLUCOSIDASE (Cytochemistry of Macrophage)
• Microspectrophotometric characterization of stained blood cells
• Histological and Biochemical Studies on Glycogenosis Type II Induced by the Injection of an Acid Aloha-Glucosidase Inhibitor
• CYTOPHOTOMETRIC DETERMINATION OF GLUTAMIC DEHYDROGENASE ACTIVITY IN MOUSE BRAIN BY USING TRIDENSITY-AUTOMICROPHOTOMETER
• Kinetics of Base Catalyzed Chemiluminescence Reaction of Spiro[adamantane -1,3'-(4'-(m-hydroxyphenyl)-4'-methoxy-1',2'-dioxetane)]
• FORMATION OF GLYCOGENOSOMES IN RAT LIVER INDUCED BY INJECTION OF ACARBOSE, AN α-GLUCOSIDASE INHIBITOR
• The Radiation-induced Addition of Hydrogen Sulfide to Propylene
• The Radiation-induced Reaction of Benzyl Mercaptan and p-Tolyl Mercaptan in Various Organic Solvents
• The Formation of Sulfur Compounds in the Radiolysis of a Toluene Solution of Sulfur
• The Reactions of Cyclic Sulfilimines with Cyanide Ion and Phosphine: Evidence for Substitution on Trivalent Sulfur
• Physical properties and various reactions of thionitrites and related substances.
• Catalytic oxidation of mercaptans by iodine-hydrogen iodide system in dimethyl sulfoxide.
• Oxidative S-dealkylation reaction of sulfide catalyzed by Co(II)(bzacen).
• Enzymatic oxidation of alkyl sulfides by cytochrome P-450 and hydroxyl radical.
• Mechanisms of enzymatic S-oxygenation of thioanisole derivatives and O-demethylation of anisole derivatives promoted by both microsomes and a reconstituted system with purified cytochrome P-450.
• A New Rearrangement Reaction of Azoxybenzene with Arenesulfonyl Chloride
• The Reaction of Azoxybenzene with Acetic Anhydride
• Nucleophilic substitution on 4-methylbenzyl thiocyanate with nucleophiles.
• Mechanism of the Oxygen Exchange Reaction of n-Butyl Methyl Sulfoxide in Sulfuric Acid
• The synthesis and properties of cyclohepta(a)phenalene-6,10-, -6,12-, -7,10-, and -7,12-diones and thier dicationic and dianionic species.
• The Reaction of 3H-1,2-Benzodithiole-3-thione with Diphenyldiazomethane
• Kinetic Study of the Pyrolysis of 1- and 2-Phenylethyl Phenyl N-Tosylsulfilimines
• Sulfilimine. XVII. Syntheses and Reactions of N-Carbamoylsulfilimines
• The Reaction of Elemental Sulfur with Organic Compounds. IV. The Reactions of N-Arenesulfonylsulfilimine and Sulfoximine with Sulfur and Diaryl Disulfide
• Electronic Spectra of Phenanthrolinediones, Phenanthrolinones, Bipyridinediones, and Amino-Substituted Phenanthrolines.
• Synthesis of 2,9-dichloro-1,10-phenanthroline from N,N'-annelated phenanthrolinediones.
• Elimination and nucleophilic substitution on nitrogen atom. Reactions of -O-aroyl-N,N-di(p-substituted benzyl)- and O-aroyl-N-benzoyl-N-benzylhydroxylamines with various nucleophiles in dipolar aprotic solvents.
• A Novel Reduction of the O-(3,5-Dinitrobenzoyl)-N,N-(aroylary)hydroxylamines by the Cyanide Ion in Dipolar Aprotic Solvents
• Intramolecular stereospecific Pummerer reactions of aryl (substituted-methyl) sulfoxides bearing electron-withdrawing groups with acetic anhydride.
• Deoxygenation of tertiary amine oxides with carbon disulfide.
• Predominant intramolecular Pummerer reactions of substituted benzyl p-tolyl sulfoxides with acetic anhydride.
• Enzymatic oxygenation of sulfides with cytochrome P-450 from rabbit liver. Stereochemistry of sulfoxide formation.
• Unusual reaction of azoxybenzenes with p-toluenesulfonic acid in acetic anhydride.
• Oxygen-18 Scrambling Reaction of Aroyl Alkyl Carbonates
• Reinvestigation of the mechanism of the reaction of N,N-dimethylaniline N-oxide with acetic anhydride.
• Reaction of haloazoxybenzenes with sulfuric acid.
• Reaction of Sulfoxides with Acylating Reagents. IV. The Catalytic Effect of Both the Brönsted and Lewis Acids in the Oxygen Exchange Reaction of Diaryl Sulfoxides with Acetic Anhydride
• Formation and Properties of Phenylthiomethyl Radical. Anodic Oxidation of Sodium Phenylthioacetate and Thermal Decomposition of t-Butyl Phenylthioperacetate
• Reaction of Sulfoxides with Acylating Reagents. III. Mechanism of the Reactions of Phenyl Methyl Sulf oxide with Acetic Anhydride
• A cross-coupling reaction of methylsulfinylarene.
• Intermolecular Pummerer rearrangement reactions of alkyl phenyl and dialkyl sulfoxides with acetic anhydride.
• Tracer Study of the Reactions of Diphenyl Sulfone and Diphenyl Sulfoxide with Diphenyl Disulfide
• The Photochemical Degradation of Diphenyl Sulfone-1-14C
• Synthesis and reaction of 2,2'-biquinolyl.
• Thermal curtius rearrangement of N-acyl-S,S-diphenylsulfilimine.
• Catalytic reduction of sulfoxide by bromine-hydrogen bromide system.
• Nucleophilic Substitution on Trivalent Nitrogen Atom. Menschutkin Type Reaction of O-2,4-Dinitrophenylhydroxylamine with Uncharged Nucleophiles
• Pyrolysis of S-(2-(phenylthio-, phenylsulfinyl-, and phenylsufonyl)-ethyl)-N-p-tosylsulfilimine.

もっと見る 閉じる

スポンサーリンク