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Journal articles on the topic 'Nitrosobenzene'

Author: Grafiati

Published: 4 June 2021

Last updated: 17 February 2022

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1

De, Surya K., Mrinal G. Dhara, and Asok K. Mallik. "Synthesis of trans-2,3-dimethoxy-3- (phenylamino)flavanones and related compounds." Canadian Journal of Chemistry 76, no. 2 (1998): 199–204. http://dx.doi.org/10.1139/v97-219.

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trans-2,3-Dimethoxy-3-(phenylamino)flavanones (2), a new type of flavanone derivatives, are synthesized from flavanones or 2'-hydroxychalcones in two steps, the first one being a condensation with nitrosobenzenes (Ehrlich-Sachs reaction) and the second an oxidation with (diacetoxyiodo)benzene in methanol. Nitrone formation, an important side reaction of the Ehrlich-Sachs reaction, has also been exploited to synthesize 2 simply by use of an excess of nitrosobenzene in aqueous methanol. Syntheses of several analogues of 2 are also reported.Key words: trans-2,3-dimethoxy-3-(phenylamino)flavanones

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2

da Machado, Fernanda. "Nitrosobenzene." Synlett 2008, no. 19 (2008): 3075–76. http://dx.doi.org/10.1055/s-2008-1067280.

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3

CROSTON, M., J. LANGSTON, G. TAKACS, et al. "CONVERSION OF ANILINE TO AZOBENZENE AT FUNCTIONALIZED CARBON NANOTUBES: A POSSIBLE CASE OF A NANODIMENSIONAL REACTION." International Journal of Nanoscience 01, no. 03n04 (2002): 285–93. http://dx.doi.org/10.1142/s0219581x02000255.

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Aniline is oxidized to nitrosobenzene as the initial product, which undergoes further oxidation to nitrobenzene. The nitrosobenzene formation is catalyzed by functionalized multiwalled carbon nanotubes (CNT) followed by a coupling reaction between nitrosobenzene and aniline to produce azobenzene. This coupling requires close proximity of the reactants. It proceeds rapidly resulting in the UV-VIS absorption spectrum showing maxima at 327 nm and 425 nm. The nitrosobenzene yield in the presence of CNTs is controlled by the amount present in the medium. As the reaction is not catalyzed by unfuncti

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4

Brook, Adrian G., and Abraha Habtemariam. "Insertion reactions of nitrosobenzene and ketenes into silaaziridines." Canadian Journal of Chemistry 81, no. 11 (2003): 1164–67. http://dx.doi.org/10.1139/v03-001.

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Nitrosobenzene, trimethylsilyl ketene, and diphenylketene insert into the ring of silaaziridines to yield relatively unstable 5-membered heterocyclic ring systems. The new compounds, which have been characterized by 1H, 13C, and 29Si NMR spectroscopy, arise from two different modes of insertion into the ring SiN bond, leading to compounds with an exocyclic C=N bond (from nitrosobenzene) or two exocyclic C=C bonds (from the ketenes).Key words: silaaziridines, ring insertion, nitrosobenzene, ketenes, heterocyclic rings.

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5

Bubnov, Yurii N., Dmitrii G. Pershin, Anna L. Karionova, and Mikhail E. Gurskii. "Allylboration of nitrosobenzene." Mendeleev Communications 12, no. 5 (2002): 202–3. http://dx.doi.org/10.1070/mc2002v012n05abeh001640.

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6

Niles, Stanley, and Charles A. Wight. "Photofragment spectroscopy of nitrosobenzene." Chemical Physics Letters 154, no. 5 (1989): 458–62. http://dx.doi.org/10.1016/0009-2614(89)87131-3.

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7

Matsuo, Jun-ichi, Yusuke Shima, Emiko Igarashi, and Tomoyuki Yoshimura. "Reactions of Nitrosobenzenes with Cyclobutanones by Activation with a Lewis Acid." Synlett 29, no. 06 (2017): 723–26. http://dx.doi.org/10.1055/s-0036-1588469.

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Formal [4+2] cycloaddition between 3-ethoxy-2-alkylcyclobutanones and nitrosobenzene proceeded by activation with Me3SiOTf to afford 6-alkyl-2-phenyl-2H-1,2-oxazin-5(6H)-one by regioselective cleavage of the more substituted C2–C3 bond of the cyclobutanone ring. On the other hand, reactions of 3-phenylcyclobutanones and 2-benzyloxycyclobutanone with nitrosobenzene gave γ,δ-unsaturated and cyclic hydroxamic acid derivatives, respectively, by cleavage of a cyclobutanone C1–C2 bond.

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8

Packett, Diane L., William C. Trogler, and Arnold L. Rheingold. "Molecular structure of (.mu.-.eta.1-nitrosobenzene-N)(.mu.-.eta.2-nitrosobenzene-N,O)(.eta.1-nitrosobenzene-N)tris(trimethylphosphine)diplatinum(II), a complex containing three linkage isomers of nitrosobenzene." Inorganic Chemistry 26, no. 26 (1987): 4308–9. http://dx.doi.org/10.1021/ic00273a006.

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9

He, Jing Hui, Wei Mao, Wei Chen, Kai Wu, Han Song Cheng, and Guo Qin Xu. "Resolving molecular orbitals self-decoupled from semiconductor surfaces." Chem. Sci. 5, no. 11 (2014): 4447–52. http://dx.doi.org/10.1039/c4sc01293c.

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10

Li, Huanhuan, Can Huang, Yingying Li, Weijun Yang, and Fan Liu. "Electrocatalytic reduction of trace nitrobenzene using a graphene-oxide@polymerized-manganese-porphyrin composite." RSC Advances 9, no. 39 (2019): 22523–30. http://dx.doi.org/10.1039/c9ra02932j.

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11

Williot, F., M. Bernard, D. Lucas, Y. Mugnier, and J. Lessard. "Article." Canadian Journal of Chemistry 77, no. 10 (1999): 1648–54. http://dx.doi.org/10.1139/v99-194.

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The electrochemical reduction of nitrosobenzene (PhNO) in the presence of cyclopentadiene derivatives containing the indenyl group represented as In'H2 (10a, 10b, and 12b) gives the imine derivatives PhN=In'. The process requires only a catalytic amount of electricity. When the electrolysis of aromatic aldehydes (ArCHO), 2,6-dichlorobenzaldehyde (1a), benzaldehyde (1b) and terephthalaldehyde (2), is performed in the presence of the In'H2 derivatives, compounds ArCH=In' are obtained in low yields. These compounds have been characterized by mass spectrometry and microanalysis. The overall proces

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12

da Silva, Anderson G. M., Daniel C. Batalha, Thenner S. Rodrigues, et al. "Sub-15 nm CeO2 nanowires as an efficient non-noble metal catalyst in the room-temperature oxidation of aniline." Catalysis Science & Technology 8, no. 7 (2018): 1828–39. http://dx.doi.org/10.1039/c7cy02402a.

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13

Zhou, Baowen, Jinliang Song, Tianbin Wu, et al. "Simultaneous and selective transformation of glucose to arabinose and nitrosobenzene to azoxybenzene driven by visible-light." Green Chemistry 18, no. 13 (2016): 3852–57. http://dx.doi.org/10.1039/c6gc00943c.

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14

Chen, Guo-Qiang, Gerald Kehr, Constantin G. Daniliuc, and Gerhard Erker. "Nitro-redox reactions at a frustrated borane/phosphane Lewis pair." Dalton Transactions 45, no. 16 (2016): 6820–23. http://dx.doi.org/10.1039/c6dt00857g.

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15

Crotti, Corrado, Chand Sishta, Andrew Pacheco, and Brian R. James. "Nitrosobenzene complexes of (octaethylporphinato)ruthenium(II)." Inorganica Chimica Acta 141, no. 1 (1988): 13–15. http://dx.doi.org/10.1016/s0020-1693(00)86366-5.

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16

Morken, J., R. Kyne, M. Ryan, and L. Kliman. "Allylation of Nitrosobenzene with Pinacol Allylboronates." Synfacts 2010, no. 12 (2010): 1406. http://dx.doi.org/10.1055/s-0030-1258859.

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17

Bleasdale, Christine, Martin K. Ellis, Peter B. Farmer, et al. "Synthesis and spectroscopic characterisation of 3-chloroperbenzoic acid-17O,18O, nitrosobenzene-17O,18O and nitrosobenzene-15N." Journal of Labelled Compounds and Radiopharmaceuticals 33, no. 8 (1993): 739–46. http://dx.doi.org/10.1002/jlcr.2580330810.

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18

Tao, Fangqi, and Qi Wang. "Aqueous radical addition-coupling polymerization using a nitroso benzene/cyclodextrin complex for the synthesis of a hydrophilic periodic polymer." RSC Advances 5, no. 57 (2015): 46007–10. http://dx.doi.org/10.1039/c5ra02371h.

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Hydrophilic periodic polymer possessing [ABxAC]n repeating sequence was synthesized by aqueous radical addition-coupling polymerization using water-soluble inclusion complex of nitrosobenzene and Me<sub>2</sub>-β-cyclodextrin.

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19

Forrester, A. R., and R. H. Thomson. "Reaction of Quinones with Nitrosoarenes." Zeitschrift für Naturforschung B 40, no. 11 (1985): 1515–18. http://dx.doi.org/10.1515/znb-1985-1117.

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The structure of the dinitrone formed on reaction of nitrosobenzene with 1,4-benzoquinone has been confirmed by spectroscopic measurements. An electron transfer radical-anion mechanism is suggested to account for its formation.

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20

Iwahashi, H., C. E. Parker, R. P. Mason, and K. B. Tomer. "Radical adducts of nitrosobenzene and 2-methyl-2-nitrosopropane with 12,13-epoxylinoleic acid radical, 12,13-epoxylinolenic acid radical and 14,15-epoxyarachidonic acid radical. Identification by h.p.l.c.-e.p.r. and liquid chromatography-thermospray-m.s." Biochemical Journal 276, no. 2 (1991): 447–53. http://dx.doi.org/10.1042/bj2760447.

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Linoleic acid-derived radicals, which are formed in the reaction of linoleic acid with soybean lipoxygenase, were trapped with nitrosobenzene and the resulting radical adducts were analysed by h.p.l.c.-e.p.r. and liquid chromatography-thermospray-m.s. Three nitrosobenzene radical adducts (peaks I, II and III) were detected; these gave the following parent ion masses: 402 for peak I, 402 for peak II, and 386 for peak III. The masses of peaks I and II correspond to the linoleic acid radicals with one more oxygen atom [L(O).]. The radicals are probably carbon-centred, because the use of 17O2 did

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21

Kohlmeyer, Corinna, Maike Klüppel, and Gerhard Hilt. "Synthesis of Nitrosobenzene Derivatives via Nitrosodesilylation Reaction." Journal of Organic Chemistry 83, no. 7 (2018): 3915–20. http://dx.doi.org/10.1021/acs.joc.8b00262.

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22

Hernán, Rodríguez C., Márquez V. Amelia та Claudio A. Chuaqui. "Reactions of α-aminoester imines with nitrosobenzene". Tetrahedron Letters 30, № 19 (1989): 2477–80. http://dx.doi.org/10.1016/s0040-4039(01)80429-9.

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23

Chainikova, E. M., A. N. Teregulova, V. A. Shamukaev, and R. L. Safiullin. "Chemiluminescence during deoxygenation of nitrosobenzene with triphenylphosphine." High Energy Chemistry 43, no. 2 (2009): 147–48. http://dx.doi.org/10.1134/s0018143909020143.

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24

Huang, Jian-Hua, Guang-Jun Wang, Xi-Bin Gu, Ke-Li Han, and Guo-Zhong He. "Photodissociation of Nitrosobenzene (C6H5NO) at 266 nm." Journal of Physical Chemistry A 104, no. 45 (2000): 10079–84. http://dx.doi.org/10.1021/jp993526i.

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25

Wu, Y. M., L. Y. Hu, and C. H. Cheng. "Phenylazoalkanes from reaction of nitrosobenzene with alkylamines." Journal of Organic Chemistry 50, no. 3 (1985): 392–94. http://dx.doi.org/10.1021/jo00203a024.

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26

Pokluda, Adam, Michal Kohout, Josef Chudoba, Martin Krupička, and Radek Cibulka. "Nitrosobenzene: Reagent for the Mitsunobu Esterification Reaction." ACS Omega 4, no. 3 (2019): 5012–18. http://dx.doi.org/10.1021/acsomega.8b03551.

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27

Zuman, Petr, and Bhavdeep Shah. "Addition, Reduction, and Oxidation Reactions of Nitrosobenzene." Chemical Reviews 94, no. 6 (1994): 1621–41. http://dx.doi.org/10.1021/cr00030a007.

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28

Kundu, Subrata, S. Chantal E. Stieber, Maryline G. Ferrier, Stosh A. Kozimor, Jeffery A. Bertke, and Timothy H. Warren. "Redox Non-Innocence of Nitrosobenzene at Nickel." Angewandte Chemie 128, no. 35 (2016): 10477–81. http://dx.doi.org/10.1002/ange.201605026.

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29

Kundu, Subrata, S. Chantal E. Stieber, Maryline G. Ferrier, Stosh A. Kozimor, Jeffery A. Bertke, and Timothy H. Warren. "Redox Non-Innocence of Nitrosobenzene at Nickel." Angewandte Chemie International Edition 55, no. 35 (2016): 10321–25. http://dx.doi.org/10.1002/anie.201605026.

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30

Uršić, S., S. Luterotti, and D. Ljubas. "Partial multifactorial design in modelling of UV-spectrometric assays of ascorbic acid with nitrosobenzene and p -nitro-nitrosobenzene." Fresenius' Journal of Analytical Chemistry 369, no. 7-8 (2001): 719–26. http://dx.doi.org/10.1007/s002160100702.

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31

Golly, I., and P. Hlavica. "N-Oxidation of 4-chloroaniline by prostaglandin synthase. Redox cycling of radical intermediate(s)." Biochemical Journal 226, no. 3 (1985): 803–9. http://dx.doi.org/10.1042/bj2260803.

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4-Chloroaniline undergoes N-oxidation in ram seminal-vesicle microsomal preparations supplemented with arachidonic acid to yield N-(4-chlorophenyl)-hydroxylamine and 1-chloro-4-nitrosobenzene. H2O2 also supports metabolism of the amine substrate to the same organic-solvent-extractable products, suggesting that the hydroperoxidase activity of prostaglandin synthase is responsible for the co-oxidation. Analysis of the reaction mixtures by e.s.r. spectrometry reveals the formation of a radical intermediate bearing the characteristics of a strongly immobilized nitroxide. Arylamine-stimulated O2.-

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32

Núñez-Vergara, Luis J., J. A. Squella, C. Olea-Azar, S. Bollo, P. A. Navarrete-Encina, and J. C. Sturm. "Nitrosobenzene: electrochemical, UV-visible and EPR spectroscopic studies on the nitrosobenzene free radical generation and its interaction with glutathione." Electrochimica Acta 45, no. 21 (2000): 3555–61. http://dx.doi.org/10.1016/s0013-4686(00)00477-1.

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33

Lin, Cheng-Tung, Li-Wei Din, and Sue-Lein Wang. "Reinvestigation of Cycloaddition of Nitrosobenzene towards 1,3-Diphenylisobenzofurans." HETEROCYCLES 29, no. 2 (1989): 263. http://dx.doi.org/10.3987/com-89-4826.

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34

Chen, Yu-Feng, Jing Chen, Li-Jen Lin, and Gary Jing Chuang. "Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzene." Journal of Organic Chemistry 82, no. 21 (2017): 11626–30. http://dx.doi.org/10.1021/acs.joc.7b01887.

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35

Giumanini, Angelo G., Nicoletta Toniutti, Giancarlo Verardo, and Marcello Merli. "Reaction of Nitrosobenzene with 4-Methoxy-N-methyleneaniline." European Journal of Organic Chemistry 1999, no. 1 (1999): 141–43. http://dx.doi.org/10.1002/(sici)1099-0690(199901)1999:1<141::aid-ejoc141>3.0.co;2-u.

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36

M. Firoze Khan, G. A. S. Ansari. "CONTRIBUTION OF NITROSOBENZENE TO SPLENIC TOXICITY OF ANILINE." Journal of Toxicology and Environmental Health, Part A 60, no. 4 (2000): 263–73. http://dx.doi.org/10.1080/00984100050027815.

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37

Tseng, Cheng-Ming, Y. M. Choi, Cheng-Liang Huang, Chi-Kung Ni, Yuan T. Lee, and M. C. Lin. "Photodissociation of Nitrosobenzene and Decomposition of Phenyl Radical†." Journal of Physical Chemistry A 108, no. 39 (2004): 7928–35. http://dx.doi.org/10.1021/jp049425o.

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38

Dvořák, Dalimil, Miloš Buděšínský, David Šaman, and Zdeněk Arnold. "Benzylidenemalonaldehydes: A redox reaction during the attempted cycloaddition on nitrosobenzene." Collection of Czechoslovak Chemical Communications 50, no. 10 (1985): 2260–64. http://dx.doi.org/10.1135/cccc19852260.

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Reaction of p-chlorobenzylidenemalonaldehyde with nitrosobenzene represents a reduction-oxidation process leading to 2-formyl-3-anilino-3-(4-chlorophenyl)acrylic acid (III). The structure of the product, including two intramolecular hydrogen bonds, has been proved by analysis of the 1H and 13C NMR spectra of the acid III, its deuterated form and the methyl ester obtained by reaction with diazomethane.

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39

Yoshioka, T., and T. Uematsu. "Formation of N-hydroxy-N-arylacetamides from nitroso aromatic compounds by the mammalian pyruvate dehydrogenase complex." Biochemical Journal 290, no. 3 (1993): 783–90. http://dx.doi.org/10.1042/bj2900783.

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Bovine, human and porcine heart mitochondria and isolated porcine heart pyruvate dehydrogenase complex (PDHC) pyruvate-dependently form N-hydroxy-N-arylacetamides from nitroso aromatic compounds, including carcinogenic 4-biphenyl and 2-fluorenyl derivatives. The PDHC-catalysed formation of N-hydroxyacetanilide (N-OH-AA) from nitrosobenzene (NOB), through a Ping Pong mechanism, is optimum at pH 6.8 and is accelerated by thiamin pyrophosphate, but is inhibited by thiamin thiazolone pyrophosphate and ATP. Km pyruvate in the reaction is independent of pH over the range tested, whereas KmNOB increa

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40

Iwahashi, H., A. Ikeda, Y. Negoro, and R. Kido. "Detection of radical species in haematin-catalysed retinoic acid 5,6-epoxidation by using h.p.l.c.-e.p.r. spectrometry." Biochemical Journal 236, no. 2 (1986): 509–14. http://dx.doi.org/10.1042/bj2360509.

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E.p.r. signals were detected in an all-trans-retinoic acid/haematin incubation mixture by using an e.p.r. spin-trapping technique. The spin adducts are presumably attributable to some intermediates in haematin-catalysed retinoic acid 5,6-epoxidation, since addition of nitrosobenzene to the reaction mixture dose-dependently inhibited the epoxidation. Analysing the reaction mixture by h.p.l.c.-e.p.r. spectrometry resulted in the detection of three peaks (III–1, III–2, IV) ascribable to the radical species. Two (peaks III–1 and −2) of the three peaks, which appeared 10 min after the reaction had

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41

List, Benjamin, Grigory Shevchenko та Stefanie Dehn. "Brønsted Acid Mediated Direct α-Hydroxylation of Cyclic α-Branched Ketones". Synlett 29, № 17 (2018): 2298–300. http://dx.doi.org/10.1055/s-0037-1610292.

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We report a Brønsted acid mediated direct α-hydroxylation of cyclic α-branched ketones via a tandem aminoxylation/N–O bond-cleavage process. Nitrosobenzene is used as the oxidant and subsequently promotes the liberation of the free alcohol. The desired products could be isolated in moderate to good yields at a maximum tested scale of 10 mmol. Derivatizations of the obtained products are presented.

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42

Keussen, Ch, U. Andresen, and H. Dreizler. "14N Quadrupole Coupling in the Rotational Spectrum of Nitrosobenzene." Zeitschrift für Naturforschung A 43, no. 4 (1988): 385–87. http://dx.doi.org/10.1515/zna-1988-0414.

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Abstract As the technique of microwave Fourier transform (MWFT) spectroscopy was improved in the recent years we give a reinvestigation of the 14N nuclear quadrupole hyperfine structure of nitroso benzene.

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43

Montanari, Stefano, Cristina Paradisi, and Gianfranco Scorrano. "Pathways of Nitrosobenzene Reduction by Thiols in Alcoholic Media." Journal of Organic Chemistry 64, no. 10 (1999): 3422–28. http://dx.doi.org/10.1021/jo981889t.

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44

Neidlinger, Andreas, Torben Kienz, and Katja Heinze. "Spin Trapping of Carbon-Centered Ferrocenyl Radicals with Nitrosobenzene." Organometallics 34, no. 21 (2015): 5310–20. http://dx.doi.org/10.1021/acs.organomet.5b00778.

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45

Biljan, Ivana, Marko Kralj, Tea Mišić Radić, Vesna Svetličić, and Hrvoj Vančik. "Dimerization of Nitrosobenzene Derivatives on an Au(111) Surface." Journal of Physical Chemistry C 115, no. 41 (2011): 20267–73. http://dx.doi.org/10.1021/jp206547k.

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46

Montanari, Stefano, Fiona O'Carroll, Cristina Paradisi, Gianfranco Scorrano, and Pietro Traldi. "Fast-atom bombardment analysis of a nitrosobenzene-thiol adduct." Rapid Communications in Mass Spectrometry 9, no. 11 (1995): 1081–82. http://dx.doi.org/10.1002/rcm.1290091121.

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47

ZUMAN, P., and B. SHAH. "ChemInform Abstract: Addition, Reduction, and Oxidation Reactions of Nitrosobenzene." ChemInform 26, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199501311.

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48

Favre, Thomas L. F., Peter J. Seijsener, Patricia J. Kooyman, Annemarieke Maltha, Adrianus P. Zuur, and Vladimir Ponec. "Selective reduction of nitrobenzene to nitrosobenzene on oxidic catalysts." Catalysis Letters 1, no. 12 (1988): 457–60. http://dx.doi.org/10.1007/bf00766206.

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49

Di Girolamo, Francesco, Luigi Campanella, Roberto Samperi, and Angela Bachi. "Mass spectrometric identification of hemoglobin modifications induced by nitrosobenzene." Ecotoxicology and Environmental Safety 72, no. 5 (2009): 1601–8. http://dx.doi.org/10.1016/j.ecoenv.2008.09.006.

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50

Roth-Barton, Jesse, and Jonathan M. White. "X-ray Structural Analysis for the Prediction on the Nature of the Retro Diels - Alder Pathway: Concerted or Stepwise. Structural Studies on Nitrosobenzene Cycloadducts." Australian Journal of Chemistry 62, no. 12 (2009): 1695. http://dx.doi.org/10.1071/ch09349.

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Crystal structures of nitrosobenzene cycloadducts 5–7 reveal structural effects consistent with the early stages of the retro Diels–Alder fragmentation. There is a clear differentiation between the structure parameters of cycloadduct 5, which reacts by a concerted synchronous pathway and that of cycloadduct 6, which must react by a two-step pathway. Based on these data, cycloadduct 7 is predicted to react by a highly asynchronous or two-step pathway.

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