Diazotization of nitroanthranilic acids. Effect of carboxyl group on the nucleophilic ipso substitution of the nitro group by chloride ion

1979 ◽  
Vol 44 (19) ◽  
pp. 3342-3344 ◽  
Author(s):  
Akira Oku ◽  
Akira Matsui
Keyword(s):  
Nitro Group ◽  
Chloride Ion ◽  
Carboxyl Group ◽  
Ipso Substitution

scholarly journals THE REACTION BETWEEN 2,2-DIPHENYL-1-PICRYLHYDRAZYL FREE STABLE RADICAL AND N-BROMOSUCCINIMIDE

1998 ◽  
Vol 6 (7) ◽  
pp. 101-106
Author(s):  
Petre Ionita
Keyword(s):  
Nitro Group ◽  
Stable Radical ◽  
Starting Material ◽  
Secondary Product ◽  
Ipso Substitution

The reactions of 2,2-diphenyl-1-picrylhydrazyl (DPPH) or 2,2-diphenyl-1-picrylhidrazine (DPPH-H) with N-bromosuccinimide (NBS) were studied. Two main compounds Br-DPPH and (Br)2 DPPH were obtained, by bromination of the starting material in para-phenyl position, and also a secondary product, N02 DPPH. It was shown that the reactions of NBS with DPPH include a substitution at the picryl group of PPH with liberation in situ of N02 (ipso-substitution of a nitro group with bromine) and subsequently N02 is scavenged by DPPH with the foundation of N02 DPPH.

Reductive Condensation of a Nitro Group with Carboxylic Acids Promoted by Phosphorus(III) Compounds: A Short Route to 5H-Dibenzo[b,e][1,4]diazepin-11(10H)-ones

Synthesis ◽  
2020 ◽  
Author(s):  
Zbigniew Wróbel ◽  
Michał Tryniszewski ◽  
Robert Bujok ◽  
Roman Gańczarczyk
Keyword(s):  
Nitro Group ◽  
Carboxylic Acids ◽  
Carboxyl Group ◽  
Short Route ◽  
Step Method ◽  
One Pot ◽  
Aryl Group ◽  
Intramolecular Condensation ◽  
Reductive Condensation

Tributyl- or triphenylphosphine promotes a one-pot, three-step method for the synthesis of differently substituted dibenzodiazepinones from N-aryl-2-nitroanilines. Pyridine analogues and the corresponding thiazepinones can also be formed using this method. The process involves deoxygenation of the nitro group, then formation of an iminophosphorane intermediate and its intramolecular condensation with a carboxyl group placed in the N-aryl group. The role of the carboxyl group in the formation of the iminophosphorane and the mode of cyclization are discussed.

Oxidative cyclizations. VI. Mechanism of cyclization of N-chloro-2-nitroanilines to benzofuroxans under alkaline conditions

1984 ◽  
Vol 37 (2) ◽  
pp. 341 ◽  
Author(s):  
KJ Chapman ◽  
LK Dyall ◽  
LK Frith
Keyword(s):  
Nitro Group ◽  
Chloride Ion ◽  
Butyl Alcohol ◽  
Oxidative Cyclizations ◽  
Alkaline Conditions ◽  
Ccl4 Solution ◽  
Conjugate Base

An improved synthesis of N-chloro-2-nitroanilines used chlorine in CCl4 solution to halogenate the 2-nitroaniline. Treatment of these CCl4 solutions of the N-chloroamines with methanolic lithium methoxide, or potassium t-butoxide in t-butyl alcohol, produced a transient red colour, and quantitative yields of the corresponding benzofuroxan (benzofurazan 1-oxide) were obtained. U.v. and e.s.r. spectra indicated that the red species is the conjugate base of the N-chloroamine. On the basis of rate measurements, it is concluded that this red anion ejects chloride ion irreversibly to yield a singlet ortho-nitrophenylnitrene, which then rapidly cyclizes to the benzofuroxan. The ortho-nitro group does not assist in chloride ion ejection.

Reaction of 5-nitro-octaethylporphyrins with nucleophiles

2002 ◽  
Vol 06 (11) ◽  
pp. 685-694 ◽  
Author(s):  
Maxwell J. Crossley ◽  
Lionel G. King ◽  
Simon M. Pyke ◽  
Charles W. Tansey
Keyword(s):  
Electron Transfer ◽  
Nitro Group ◽  
Transfer Reactions ◽  
Nucleophilic Attack ◽  
Grignard Reagents ◽  
Free Base ◽  
Lower Efficiency ◽  
Electron Transfer Reactions ◽  
Ipso Substitution ◽  
Two Factors

An investigation of the reactions of metallo-5-nitro-2,3,7,8,12,13,17,18-octaethylporphyrins with Grignard reagents, benzyl oxide, phenoxide and benzenethiolate nucleophiles shows that, except for benzenethiolate reactions, they are less efficient than related reactions of metallo-2-nitro-5,10,15,20-tetraarylporphyrins. Treatment of free-base and nickel(II) 5-nitro-octaethylporphyrin with the “soft” nucleophile benzenethiolate in DMF affords the corresponding 5-phenylthioporphyrins in 61 and 72% yield, respectively, by ipso-substitution of the nitro group. In contrast, with methylmagnesium iodide and benzyl oxide, “hard” nucleophiles, attack is at the diagonally opposite 15-position of the ring to give 15-substituted 5-nitroporphyrin while with phenoxide and more substituted Grignard reagents, electron-transfer reactions lead to denitration to (metallo)-octaethylporphyrin or reduction to the corresponding 5-aminoporphyrin. The lower efficiency of the latter reactions, compared to those on 2-nitro-tetraarylporphyrin analogues, is a consequence of two factors, higher energies being required for initial nucleophilic attack as macrocyclic aromaticity is lost in intermediates and the susceptibility of the resultant “non-aromatic” intermediates to further attack.

Structural Study of a new Compound Based on Acid 1,4-Cyclohexanedicarboxylic (1,4-CDC)

2010 ◽  
Vol 6 (1) ◽  
pp. 891-896
Author(s):  
Manel Halouani ◽  
M. Dammak ◽  
N. Audebrand ◽  
L. Ktari
Keyword(s):  
Aqueous Solution ◽  
Water Molecules ◽  
Carboxyl Group ◽  
X Ray Diffraction ◽  
Compound I ◽  
Unit Cell Parameters ◽  
Monoclinic System ◽  
X Ray ◽  
Cell Parameters ◽  
Cyclohexanedicarboxylic Acid

One nickel 1,4-cyclohexanedicarboxylate coordination polymers, Ni2 [(O10C6H4)(COO)2].2H2O  (I), was hydrothermally synthesized from an aqueous solution of Ni (NO3)2.6H2O, (1,4-CDC) (1,4-CDC = 1,4-cyclohexanedicarboxylic acid) and tetramethylammonium nitrate. Compound (I) crystallizes in the monoclinic system with the C2/m space group. The unit cell parameters are a = 20.1160 (16) Å, b = 9.9387 (10) Å, c = 6.3672 (6) Å, β = 97.007 (3) (°), V= 1263.5 (2) (Å3) and Dx= 1.751g/cm3. The refinement converged into R= 0.036 and RW = 0.092. The structure, determined by single crystal X-ray diffraction, consists of two nickel atoms Ni (1) and Ni (2). Lots of ways of which is surrounded by six oxygen atoms, a carboxyl group and two water molecules.

NAS 825

Alloy Digest ◽  
2012 ◽  
Vol 61 (2) ◽  
Keyword(s):  
Corrosion Resistance ◽  
Physical Properties ◽  
Stress Corrosion ◽  
Tensile Properties ◽  
Nickel Alloy ◽  
Stress Corrosion Cracking ◽  
Chloride Ion ◽  
Heat Treating ◽  
Corrosion Cracking ◽  
Corrosion Resistant

Abstract NAS 825 is a corrosion-resistant nickel alloy that has resistance to both oxidizing and reducing environments, and with 42% nickel, the alloy is very resistant to chloride-ion stress-corrosion cracking. This datasheet provides information on composition, physical properties, hardness, elasticity, and tensile properties. It also includes information on corrosion resistance as well as forming, heat treating, machining, and joining. Filing Code: Ni-694. Producer or source: Nippon Yakin Kogyo Company Ltd.

SANDMEYER ALLOY 825

Alloy Digest ◽  
2011 ◽  
Vol 60 (2) ◽  
Keyword(s):  
Fracture Toughness ◽  
Corrosion Resistance ◽  
Physical Properties ◽  
Stress Corrosion ◽  
Nickel Alloy ◽  
Stress Corrosion Cracking ◽  
Chloride Ion ◽  
Heat Treating ◽  
Steel Company ◽  
Good Corrosion Resistance

Abstract Sandmeyer alloy 825 is a nickel alloy high in chromium and molybdenum with good corrosion resistance and ductility. The alloy has enough nickel (42%) to be relatively free from chloride-ion stress-corrosion cracking. This datasheet provides information on composition, physical properties, hardness, and tensile properties as well as fracture toughness. It also includes information on corrosion resistance as well as forming, heat treating, and joining. Filing Code: Ni-687. Producer or source: Sandmeyer Steel Company.

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