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Isao Yamaguchi Yukako Tsuse 《Journal of polymer science. Part A, Polymer chemistry》2014,52(4):481-492
Polythiophenes with reactive Zincke salt structure, P4ThPy+DNP(Cl?)‐a and P5ThPy+DNP(Cl?)‐a , were synthesized by the oxidation polymerization of oligothiophenes, such as 3'‐(4‐N‐(2,4‐dinitrophenyl)pyridinium chloride)?2,2':5',2'';5'',2'''‐quarterthiophene ( 4ThPy+DNP(Cl?) ) and 4''‐(4‐N‐(2,4‐dinitrophenyl)pyridinium chloride)?2,2';5',2'';5'',2''';5''',2''''‐quinquethiophene ( 5ThPy+DNP(Cl?) ), with iron(III) chloride. The reaction of P5ThPy+DNP(Cl?)‐a with R‐NH2 [R = n‐hexyl (Hex) and phenyl (Ph)] substituted the 2,4‐dinitrophenyl group into the R group with the elimination of 2,4‐dinitroaniline to yield P5ThPy+R(Cl?) . Similarly, model compounds, 4ThPy+R(Cl?) and 5ThPy+R(Cl?) (R = Hex and Ph), were also synthesized. In contrast to the photoluminescent 4ThPy and 5ThPy , the compounds P4ThPy+DNP(Cl?)‐a , P5ThPy+DNP(Cl?)‐a , and P5ThPy+R(Cl?) showed no photoluminescence because their internal pyridinium rings acted as quenchers. Cyclic voltammetry measurements suggested that P4ThPy+DNP(Cl?)‐a , P5ThPy+DNP(Cl?)‐a , and P5ThPy+R(Cl?) received an electrochemical reduction of the pyridinium and 2,4‐dinitrophenyl groups and oxidation of the polymer backbone. P4ThPy+DNP(Cl?)‐a and P5ThPy+DNP(Cl?)‐a were electrically conductive (ρ = 3.0 × 10 ? 6 S cm ? 1 and 2.1 × 10 ? 6 S cm ? 1, respectively) in the nondoped state. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 481–492 相似文献
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Marcos Caroli Rezende Ingrid PonceRubén Oñate Iriux AlmodovarCarolina Aliaga 《Tetrahedron letters》2014
The reaction between N-(2,4-dinitrophenyl)-4-(4-pyridyl)pyridinium chloride and 4-aminothiophenol led to an unexpected displacement of the 2,4-dinitrophenyl group, in contrast with the normal Zincke product formed with other nucleophilic 4-substituted anilines. Evidence for a SET process was obtained from EPR spectra of the reaction mixture. 相似文献
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N. O. Mahmoodi M. Mamaghani A. Ghanadzadeh M. Arvand M. Fesanghari 《Journal of Physical Organic Chemistry》2010,23(3):266-270
Synthesis of several ‘dyes’, analogs of retinal imine visual pigment via nucleophilic attack of some secondary amines to pyridinium salts following precyclic ring‐opening reaction, is discussed. The photochromic properties of these dyes have been studied by UV‐Vis spectroscopy under irradiation of UV light. Copyright © 2009 John Wiley & Sons, Ltd. 相似文献
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The synthesis of Arctic sponge alkaloid viscosaline (1) is achieved by using the Zincke reaction as the penultimate step. A key synthetic intermediate theonelladin C (6), itself a marine sponge natural product, is synthesised efficiently using a four-step sequence. 相似文献
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3-Aminocoumarines and 2-iminochromen-3-amines were efficiently prepared from the Zincke-ring-opening reaction of the corresponding 2H-chromen-3-pyridinium chlorides using N-methylpiperazine. This methodology unravels the marked potential of pyridinium salts as protective groups for primary amines. 相似文献
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Dr. Stefano Carella Dr. Misal Giuseppe Memeo Prof. Paolo Quadrelli 《ChemistryOpen》2019,8(9):1209-1221
1,2,4-Oxadiazole[4,5-a]piridinium chloride adds nucleophiles to undergo electrocyclic ring opening affording 1,2,4-oxadiazole dienamino derivatives. These pyridinium salts represent a special class of Zincke salts that are prone to rearrange when treated with primary amines or in the presence of bicarbonate to give the pyridones. The pivotal tuning of the experimental conditions leads to a straightforward synthesis of valuable 1,2,4-oxadiazole dienamine derivatives. The mechanism is also discussed in the light of NMR experiments and theoretical calculations. 相似文献
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Isao Yamaguchi Takuya Nakahara 《Journal of polymer science. Part A, Polymer chemistry》2012,50(16):3340-3349
Polythiophenes with reactive Zincke salt structure, such as PThThPy+DNP(Cl?)Th , were synthesized by the oxidation polymerization of 3′‐(4‐N‐(2,4‐dinitrophenyl)pyridinium chloride)‐2,2′:5′,2″‐terthiophene ( ThThPy+DNP(Cl?)Th ) with iron(III) chloride or copper(II) trifluoromethanesulfonate. The reaction of PThThPy+DNP(Cl?)Th with R‐NH2 (R = n‐hexyl (Hex) and phenyl (Ph)) substituted the 2,4‐dinitrophenyl group into the R group with the elimination of 2,4‐dinitroaniline to yield PThThPy+R(Cl?)Th . Similarly, model compounds, ThThPy+R(Cl?)Th (R = Hex and Ph), were also synthesized. In contrast to the photoluminescent ThThPyTh and PThThPyTh , the compounds PThThPy+DNP(Cl?)Th , PThThPy+R(Cl?)Th , and ThThPy+R(Cl?)Th showed no photoluminescence because their internal pyridinium rings acted as quenchers. Cyclic voltammetry measurements suggested that PThThPy+DNP(Cl?)Th received an electrochemical reduction of the pyridinium and 2,4‐dinitrophenyl groups and oxidation of the polymer backbone. PThThPy+DNP(Cl?)Th was electrically conductive (ρ = 2.0 × 10?6 S cm?1) in the non‐doped state. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 相似文献
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1,2,4-Oxadiazole[4,5-a]piridinium salts add alcohols and alkoxides to undergo electrocyclic ring opening affording alkoxybutadienyl 1,2,4-oxadiazole derivatives. The pyridinium salts represent a special class of Zincke salts that are prone to rearrange to give alkoxybutadienyl 1,2,4-oxadiazoles when treated with suitable nucleophiles or, alternatively, to give pyridones in the presence of bicarbonate. The pivotal tuning of the experimental conditions leads to a straightforward synthesis of valuable 1,2,4-oxadiazole derivatives. The mechanism is also discussed in the light of previous observations. 相似文献
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