The Preparation of Naphthidine

Cohen, S.C.; Oesper, Ralph E.

doi:10.1021/ac50102a036

Cited by 11 publications

(10 citation statements)

References 12 publications

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“…N ‐Methylpyrrolidone (NMP) purchased from Wako Pure Chemical Industries was dried over calcium hydride and distilled under nitrogen. 1,1′‐Diamino‐2,2′‐binaphthyl was prepared according to previous reports …”

Section: Methodsmentioning

confidence: 99%

Improvement in semipermeable membrane performance of wholly aromatic polyamide through an additive processing strategy

Aiba

Tokuyama

Baba

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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A new concept for the method to provide semipermeability in ultrathin and single-component wholly aromatic polyamide membranes has been developed for the first time. It was found that water molecules could permeate through the membrane prepared not from polyamides containing flexible ether, bulky binaphthyl, or fluorene rigid units, but one with carboxylic acid groups under a reverse osmosis mode. However, the enhancement of water transport properties by introducing the hydrophilic group of polyamide was not substantial. Therefore, polyamide membranes were prepared from the solution containing aqueous additives in order to weaken hydrogen bonds between polymer chains and thereby to suppress the aggregation of the polymer chains. As a result, water flux was dramatically improved with slightly improved NaCl rejection. Our analyses based on attenuated total reflectance Fourier transform infrared spectroscopy and solid-state carbon polarization and magic angle spinning nuclear magnetic resonance ( 13 C CPMAS NMR) spectroscopy confirmed that the aggregation of polymer chains due to the hydrogen bonds among the amide linkages was suppressed by the coordination of the aqueous additives to the amide linkage. The state of water in the membranes analyzed by differential scanning calorimetry also supported the formation of pores.

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Section: Methodsmentioning

confidence: 99%

Improvement in semipermeable membrane performance of wholly aromatic polyamide through an additive processing strategy

Aiba

Tokuyama

Baba

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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“…98-99', 790m, 750w, 730w, 720m, 690~2, 660~1, 600w, 570m, 540w, 520n, 430w, 340w, 300~1, 250w. Dijnaphthalen-l-yl)diazeiie (2) [36]. To a vigorously stirred suspension of naphthalen-1-amine ( 1 ; 9.50 g, 66.3 mmol) in H,O (200 ml) and conc.…”

Section: Experimental Partmentioning

confidence: 99%

“…The org. phase was dried (Na,SO,) and evaporated to yield a yellow solid which was sublimated at 5O"/high vacuum: 3 Dijnaphthalen-l-yl)diazeiie (2) [36]. To a vigorously stirred suspension of naphthalen-1-amine ( 1 ; 9.50 g, 66.3 mmol) in H,O (200 ml) and conc.…”

Section: Experimental Partmentioning

confidence: 99%

“…Scheme 1 Ejfect of Temperature on the Regzo~electrvity of the Cyclopalladatron of Aromatic Schiff Bayer [21] HC/" [35], the cyclometalland 1 ,l'-azonaphthalene (2) was synthesized by diazotization of naphthalen-1-amine (1) and subsequent treatment of the diazonium solution with sodium acetate and sodium sulfite [36]. Although the yield (59 %) was moderate, this method is still preferable to, e.g., the reduction of l-nitronaphthalene [37] [38] which usually yields even lower amounts of the symmetrical coupling product.…”

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confidence: 99%

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Cyclopalladation of 1,1′‐Azonaphthalene (= Di(naphthalen‐1‐yl)diazene): Isolation and characterization of two isomeric complexes

Kind¹,

Klaus²,

Rys³

et al. 1998

Helvetica Chimica Acta

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The cyclopalladation of 1 ,l'-azonaphthalene (= di(naphtha1en-I -yl)diazene; 2) with bis(hexafluoroacety1-acetonato)palladium(II) (3; [Pd(hfa),]) yields the ortho-palladated complex (1,1,1,5,5,5-hexafluoropentane-2,4-dionato-fc20,0')[i -(naphthalen-l-ylaro-~~2)naphthalen-2-yl-~Cz]palladium(II) (4) as well as the peri-palladated complex (1,1,1,5,5,5-hexafluoropentane-2,4-d~onato-~~0,O)[8-(naphthalen-l-ylazo-~~~)naphthalen-l-yl-~C']-palladium(I1) (5); their structures were corroborated by X-ray analyses. The formation of the novel peri-metallated product 5 containing a six-membered palladacycle strongly depends upon the reaction conditions.Introduction. -The cyclometallation reaction -albeit described for the first time some 25 years ago [l] [2] -still has an enormous potential as a synthetic tool when employed for the ortho-functionalization of suitable arenes [3 -81. Only recently, cyclopalladated complexes were described that catalyze the Heck olefination [9] or aryl-coupling reactions [lo] in homogeneous solution with high turnover numbers. Other cyclopalladated complexes exhibit some promising liquid-crystalline [ l l -131 or photochemical and electrochemical [14-161 properties. The cyclometallation principle can also be applied effectively to the laboratory-scale syntheses of dyestuff molecules and dyestuff precursors [17].Whereas the papers on investigations of the C-H activation at phenylic ortho-positions 'are copious, far less has been reported on the cyclometallation of naphthalene moieties so far [6][18-281, despite the fact that the naphthalene ring is more reactive towards electrophilic cyclometallating agents. Furthermore, naphthalenes with donorbearing substituents at C( 1) offer both the ortho-and the peri-position for the cyclometallation.To make 1-substituted naphthalenes like naphthalen-1-amine (1) amenable to cyclopalladation, they have to be converted into suitable donor-bearing cyclometallands, as, e.g., the corresponding 1 ,If-azonaphthalene (= di(naphtha1en-1-y1)diazene ; 2). Transforming the original naphthalen-1-amine (1) into the symmetrical 1 ,l'-azonaphthalene (2) has several advantages: this cyclometalland is providing a donor atom for each of the two naphthalene moieties, and the desired functional groups can be introduced into both rings by two separate metallation/cleavage sequences. Finally, the bis-ortho-substituted azonaphthalene would yield two identical ortho-functionalized naphthalen-1-amines upon complete reduction of the azo bridge.The cyclopalladation of the unsubstituted 1 ,l'-azonaphthalene (2) is expected to occur at the C(2) center ortho to the azo bridge, as was shown earlier for various 1 -(phenylazo)naphthalenes [26] [27]. There, the naphthalene peri-position (C(8)) was only

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“…6 was prepared by the Schiemann reaction of 4,4 0 -diamino-1,1 0 -binaphthyl (Scheme 2A), which was synthesized from 1-aminonaphthalene by a diazonium coupling reaction, followed by reduction, and transfer reaction. 21 6 was characterized by its 1 H and 13 C NMR spectra, 1 H COSY spectrum (ESI †), and elemental analysis. Fig.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of highly refractive poly(phenylene thioether)s containing a binaphthyl or diphenylfluorene unit

et al. 2012

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The Preparation of Naphthidine

Cited by 11 publications

References 12 publications

Improvement in semipermeable membrane performance of wholly aromatic polyamide through an additive processing strategy

Improvement in semipermeable membrane performance of wholly aromatic polyamide through an additive processing strategy

Cyclopalladation of 1,1′‐Azonaphthalene (= Di(naphthalen‐1‐yl)diazene): Isolation and characterization of two isomeric complexes

Synthesis of highly refractive poly(phenylene thioether)s containing a binaphthyl or diphenylfluorene unit

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