134-32-7Relevant articles and documents
Reactivity of 1-nitronaphthalene and 1,3-dinitronaphthalene with conjugated dienes. An easy access to N-naphthylpyrroles
Paredes, Elisa,Kneeteman, María,Gonzalez-Sierra, Manuel,Mancini, Pedro M.E.
, p. 2943 - 2945 (2003)
1-Nitronaphthalene reacts at high temperature with poor and moderately reactive dienes affording N-naphthylpyrroles while, with the same dienes, 1,3-dinitronaphthalene exhibits the dienophilic character of naphthalenic C3-C4 bond producing the corresponding phenanthrenes through a classical Diels-Alder process.
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Smolka,Halla
, p. 1146 (1901)
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Finnegan,Knutson
, p. 1670 (1968)
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Excited-State Proton-Transfer Reactions of Naphthylammonium Ion-18-Crown-6 Complexes
Shizuka, Haruo,Kameta, Kosei,Shinozaki, Tsutomu
, p. 3956 - 3963 (1985)
Proton-transfer reactions in the excited singlet state of naphthylammonium ion-18-crown-6 complexes in MeOH-H2O (9:1) mixtures have been studied by means of the single photon counting method with fluorimetry.It is found that the complex formation of naphthylammonium ions with 18-crown-6 decreases markedly the proton-transfer rate (k1) in the excited state, resulting in an increase of its lifetime.The back protonation rate in the excited state is negligibly small compared with those of the other decay processes; there is no excited-state prototropic equilibrium in the naphthylammonium ion-crown complexes (RN(1+)H3-crown).The one-way proton transfer reaction is elucidated by the presence of the excited neutral amine-crown complex (RNH2-crown)* produced by deprotonation of (RN(1+)H3-crown)*, where protonation to the amino group is structurally blocked by 18-crown-6 and the naphthyl group (R) of the complex.However, proton-induced quenching (k'q) occurs effectively especially in the 1-naphthylammonium ion-crown complex.The ground-state association constants (Kg) of the complexes can be determined easily by the fluorescence titration method.Temperature effects upon the excited-state proton-transfer reactions of the complexes have been also carried out in order to study their thermodynamic properties.A Corey-Pauling-Kolton model of the anilinium ion-18-crown-6 complex proposed by Izatt et al. is strongly supported by the present work.
Hydrolysis of naptalam and structurally related amides: Inhibition by dissolved metal ions and metal (hydr)oxide surfaces
Huang, Ching-Hua,Stone, Alan T.
, p. 4425 - 4434 (1999)
In metal ion-free solutions, the secondary amide naptalam hydrolyzes more rapidly as the pH is decreased; intramolecular nucleophilic attack by a carboxylate side group is very likely involved. Millimolar levels of dissolved Cu(II) and Zn(II) inhibit hydr
Selective optical detection of HSO4 ? via hydrolysis of a simple Schiff Base
Dong, Zhen Ming,Wang, Jia Na,Wang, Wei,Chao, Jian Bin,Wang, Yu
, p. 4001 - 4013 (2018)
A very simple Schiff Base derived from 1-Naphthylamine and 4-(Trifluoromethy) benzaldehyde (L) was prepared as a selective colorimetric and turn-on fluorescent sensor for hydrogen sulfate. In the CH3CN:H2O (3:2, v/v) solvent system, L shows a highly selective colorimetric response to HSO4 ? ions by changing its color from yellow to colorless immediately. In addition, the weakly fluorescent receptor L shows a highly selective enhancement of fluorescence intensity at 425?nm for HSO4 ? upon excitation at 320?nm. The recognition process is proven to be hardly influenced by the other tested competitive anions. The sensing is suggested to involve a hydrolysis process promoted by HSO4 ? which has been further supported by UV–Vis, 1H NMR and HRMS spectroscopic studies. Applicability of L to detect HSO4 ? in tap water has been demonstrated. An easy-to-prepare test strip of L has also been made for the naked-eye detection of HSO4 ? in real samples.
Biocatalytic Aromaticity-Breaking Epoxidation of Naphthalene and Nucleophilic Ring-Opening Reactions
Zhang, Wuyuan,Li, Huanhuan,Younes, Sabry H. H.,Gómez De Santos, Patricia,Tieves, Florian,Grogan, Gideon,Pabst, Martin,Alcalde, Miguel,Whitwood, Adrian C.,Hollmann, Frank
, p. 2644 - 2649 (2021)
Aromatic hydroxylation reactions catalyzed by heme-thiolate enzymes proceed via an epoxide intermediate. These aromatic epoxides could be valuable building blocks for organic synthesis giving access to a range of chiral trans-disubstituted cyclohexadiene
Urner,Bergstrom
, p. 2108 (1945)
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Anderson et al.
, p. 1980 (1977)
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Carroll et al.
, p. 943 (1977)
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A new access to 1-naphthylamines by an equivalent Semmler-Wolff reaction
Janin,Bisagni
, p. 57 - 59 (1993)
A new access to 1-naphthylamines from the corresponding 3,4-dihydro-1(2H)-naphthalenones (α-tetralones) is described. It proceeds in a two-step sequence: preparation of the benzyl Schiff's base of an α-tetralone followed by aromatization over palladium ca
Relationship between azo dye structure and rat hepatic azoreductase activity
Shargel,Banijamali,Kuttab
, p. 161 - 164 (1984)
The rate of reduction was determined for a variety of azo dyes using the rat hepatic azoreductase enzyme system. In decreasing order, the rates of reduction for the azo dyes expressed as nmol of arylamine product formed/min/0.25 g of liver were amaranth (33.2), azosulfamide (32.5), orange G (12.4), 1,2-dimethyl-4-p-(carboxyphenylazo)-5-hydroxybenzene (CPA) (9.27), brilliant crystal scarlet (8.00), sulfachrysoidine (7.27), and Sudan I (1.03). A comparison of the partition coefficient with its rate of reduction indicated that the water-soluble azo dyes were reduced more rapidly than the lipid-soluble ones. Furthermore, higher rates of reduction were observed for those dyes containing electron-withdrawing groups on the aromatic rings.
Rearrangement of 2-Quinolyl- and 1-Isoquinolylcarbenes to Naphthylnitrenes
Lan, Nguyen Mong,Burgard, Riko,Wentrup, Curt
, p. 2033 - 2036 (2004)
2-Quinolylcarbene 23 and 1-isoquinolylcarbene 33 are generated by flash vacuum thermolysis (FVT) of the corresponding triazolo[1,5-a]quinoline and triazolo[5,1-a]isoquinoline 19 and 29, as well as 2-(5-tetrazolyl)quinoline and 1-(5-tetrazolyl)isoquinoline 20 and 30, respectively. These carbenes rearrange to 1- and 2-naphthylnitrene 21 and 31, respectively, and the nitrenes are also generated by FVT of 1- and 2-naphthyl azides 18 and 28. The products of FVT of both the nitrene and carbene precursors are the 2- and 3-cyanoindenes 26 and 27 together with the nitrene dimers, viz. azonaphthalenes 25 and 35, and the H-abstraction products, aminonaphthalenes 24 and 34. All the azide, triazole, and tetrazole precursors yield 3-cyanoindene 26 as the principal ring contraction product under conditions of low FVT temperature (340-400 °C) and high pressure (1 Torr N2 as carrier gas for the purpose of collisional deactivation). This ring contraction reaction is strongly subject to chemical activation, which caused extensive isomerization of 3-cyanoindene to 2-cyanoindene under conditions of low pressure (10-3 Torr). 2-Cyanoindene is calculated to be ca. 1.7 kcal/mol below 3-cyanoindene in energy; accordingly, high-temperature FVT of these cyanoindenes always gives mixtures of the two compounds with the 2-cyano isomer dominating. Photolysis of trizolo[1,5-a]quinoline 19 and triazolo[5,1-a]isoquinoline 29 in Ar matrixes causes partial ring opening to the corresponding 2-diazomethylquinoline 19′ and 1-diazomethylisoquinoline 29′. The photolysis of the former gives rise to a small amount of the cyclic ketenimine 22, the intermediate connecting 2-quinolylcarbene and 1-naphthylnitrene.
Structural and Reactivity Comparisons of JosiPhos CyPF-Cy and a Simplified Variant ("CyPBn-Cy") in Nickel-Catalyzed C(sp2)-N Cross-Couplings
Bodé, Nicholas E.,Ferguson, Michael J.,Stradiotto, Mark,Tassone, Joseph P.
, p. 2915 - 2922 (2021/08/27)
The synthesis and characterization of the new complexes (CyPBn-Cy)NiCl2 and (CyPBn-Cy)Ni(o-tol)Cl are reported (CyPBn-Cy = o-di(cyclohexyl)phosphino-benzyl-di(cyclohexyl)phosphine), along with a head-to-head structural and reactivity comparison of (L)Ni(o-tol)Cl precatalyst complexes (L = JosiPhos CyPF-Cy and CyPBn-Cy) in the Ni-catalyzed cross-couplings of (hetero)aryl chlorides or phenol-derived electrophiles with ammonia or furfurylamine. The structures of these precatalysts were found not to differ significantly (e.g., coordination geometry and % buried volume), and these similarities were, generally speaking, reflected in the observed catalytic behavior of these precatalysts, with notable exceptions including reactions involving the hindered electrophile 2-chloro-m-xylene, where (CyPBn-Cy)Ni(o-tol)Cl proved superior; the N-arylation of furfurylamine by use of 1-(N,N-diethylcarbamoyl)-naphthalene, where CyPF-Cy proved to be the preferred ligand; and monoarylation (CyPBn-Cy) versus diarylation (CyPF-Cy) selectivity in the cross-coupling of furfurylamine with 2-chloro-6-methoxypyridine. In studying the time-course of the cross-coupling of furfurylamine and 1-chloronaphthalene, significantly faster conversion to product and higher overall yield were noted when using CyPBn-Cy. These results confirm that CyPBn-Cy can be viewed as being competitive with, and complementary to, the well-established JosiPhos ligand CyPF-Cy in this class of Ni-catalyzed cross-couplings.
Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?
Qiu, Xu,Wang, Yachong,Su, Lingyu,Jin, Rui,Song, Song,Qin, Qixue,Li, Junhua,Zong, Baoning,Jiao, Ning
, p. 3011 - 3016 (2021/09/13)
Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.