Chemistry of 2-aryl-1-cyano-1-nitroethenes. Part I. Synthesis and physical properties

• Autorzy: Woliński P. , Jasiński R.

Identyfikatory

DOI

10.4467/2353737XCT.18.024.7997

Warianty tytułu

PL

Chemia 2-arylo-1-cyjano-1-nitroetenów. Część I. Otrzymywanie i właściwości fizyczne

• Języki publikacji: EN

Abstrakty

EN

In this paper, we present the methodology of preparation of 2-aryl-1-cyano-1-nitroethenes and the synthesis of their main precursor – nitroacetonitrile. We have also gathered the physical properties of all compounds of this group known in the literature.

PL

W niniejszej pracy przedstawiliśmy metodologię otrzymywania 2-arylo-1-cyjano-1-nitroetenów oraz ich głównego prekursora, jakim jest nitroacetonitryl. Przedstawiliśmy również właściwości fizyczne wszystkich znanych w literaturze związków ze wspomnianej grupy.

Słowa kluczowe

EN

nitroacetonitrile; ACN; NAN; synthesis; 2-aryl-1-cyano-1-nitroethene; 3-aryl-2-nitro-2-propenenitrile

PL

nitroacetonitryl; synteza; 2-arylo-1-cyjano-1-nitroeten; 3-arylo-2-nitro-2-propenonitryl

• Wydawca: Wydawnictwo Politechniki Krakowskiej im. Tadeusza Kościuszki
• Czasopismo: Technical Transactions
• Rocznik: 2018
• Tom: Vol. 115, iss. 2
• Strony: 109--122
• Opis fizyczny: Bibliogr. 42 poz., wz., tab.

Twórcy

autor

Woliński P.

• Faculty of Chemical Engineering and Technology, Cracow University of Technology

autor

Jasiński R.

• Faculty of Chemical Engineering and Technology, Cracow University of Technology

Bibliografia

• [1] Barrett A.G.M., Graboski G.G., Conjugated nitroalkenes: versatile intermediates in organic synthesis, Chemical Reviews, 1986, 86, 751–762.
• [2] Ono N., The nitro group in organic synthesis, Wiley-VCH, Weinheim 2001.
• [3] Ballini R., Petrini M., Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction), Tetrahedron, 2004, 60, 1017–1047.
• [4] Belenkii L.I., [in:] Nitrile oxides, nitrone and nitronates in organic synthesis, Ed. H. Feuer, Wiley, 2007.
• [5] Boruwa J., Gogoi N., Saikia P.P., Barua N.C., Catalytic asymmetric Henry reaction, Tetrahedron: Asymmetry, 2006, 17, 3315–3326.
• [6] Agrawal J.P., Hodgson R.D., Chemistry of explosives, Wiley, 2007.
• [7] Bergmeier S.C., The Synthesis of Vicinal Amino Alcohols, Tetrahedron, 2000, 56, 2561–2576.
• [8] Denmark S.E., Cottell J.J., [in:] The chemistry of heterocyclic compounds, Eds. A. Padwa, W.H. Pearson, New York 2002.
• [9] Novikov C.C., Shvekhgeimer G.A., Sevastyanova V.V., Shlaposhnikov V.A., Khimiya alifaticheskikh i alitsiklicheskikh nitrosoedinenii, Khimya, Moscov 1974.
• [10] Nguyen T.B., Martel A., Gaulon-Nourry C., Dhal R., Dujardin G., 1,3-Dipolar Cycloadditions of Nitrones to Hetero-substituted Alkenes Part 2: Sila-, Thia-, Phospha- and Halo-substituted Alkenes, Organic Preparations and Procedures International, 2012, 44, 1–81.
• [11] Terrier F., Dust J.M., Buncel E., Dual super-electrophilic and Diels–Alder reactivity of neutral 10π heteroaromatic substrates, Tetrahedron, 2012, 68, 1829–1843.
• [12] Ried W., Köhler E., Königstein F.J., Reacktionen mit Nitro-acetonitril, Liebigs Annalen, 1956, 598, 145–158.
• [13] R. Jasiński, Preparatyka alifatycznych nitrozwiązków, RTN, 2013.
• [14] Matthews V.E., Kubler D.G., Improved Synthesis of Salts and Esters of Nitroacetic Acid, Journal of Organic Chemistry, 1960, 25, 266–268.
• [15] Steinkopf W., Bohrmann L., Das Nitro-acetonitril, Liebigs Annalen, 1908, 41, 1044–1052.
• [16] Kanishchev M.I., Korneeva N.V., Shevelev S.A., Synthesis of 3-amino-5-benzylamino-4-nitropyrazole, Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 1986, 35, 2145–2147.
• [17] Boguszewska-Czubara A., Lapczuk-Krygier A., Rykala K., Biernasiuk A., Wnorowski A., Popiolek L., Maziarka A., Hordyjewska A., Jasiński R., Novel synthesis scheme and in vitro antimicrobial evaluation of a panel of (E)-2-aryl-1-cyano-nitroethenes, Journal of Enzyme Inhibition and Medical Chemistry, 2016, 31, 900–907.
• [18] Jasiński R., Miroslaw B., Demchuk O.M., Babyuk D., Łapczuk-Krygier A., In the search for experimental and quantumchemical evidence for zwitterionic nature of (2E)-3-[4-(dimethylamino)phenyl]-2-nitroproprop-2-enenitrile – an extreme example of donor-π-acceptor push-pull molecule, Journal of Molecular Structure, 2016, 1108, 689–697.
• [19] Kislyi V.P., Laikhter A.L., Ugrak B.L., Semenov V.V., Synthesis of α-functional nitro compounds by the nitration of activated carbonyl compounds in a two-phase system, Russian Chemical Bulletin, 1994, 43, 70–74.
• [20] Voinkov E.K., Ulomskiy E.N., Rusinov V.L., Savateev K.V., Fedotov V.V., Gorbunov E.B., Isenov M.L., Eltsov O.S., New stable form of nitroacetonitrile, Mendeleev Communications, 2016, 26, 172–173.
• [21] Acheson R.M., Dearnaley D.P., Plunkett A.O., Porter V.C., The amino-acid Analogue of Mescaline, Journal of Chemical Sciences, 1963, 0, 2085–2087.
• [22] Мечков Ц.Д., Демирева З.И., Синтез некоторых бисаммониевых солей 2,4-динитро-3-(4-фторфенил)глутаронитрила, Журнал органической химии, 1985, 21, 1884–1887.
• [23] Baichurin R.I., Aboskalova N.I., Trukhin E.V., Berestovitskaya V.M., Aryl(hetaryl)-Containing gem-Cyanonitroethenes: Synthesis, Structure, and Reactions with 2,3-Dimethyl-1,3-butadiene, Russian Journal of General Chemistry, 2015, 85, 1845–1854.
• [24] Metchkov T., Demireva Z., Die Synthese einiger Bis-Ammoniumsalze von 3,4-Dinitro-8-(methoxyphenyl)glutarnitrilen, Zeitschrift für Chemie, 1985, 25, 169–170.
• [25] M. Kwiatkowska, Praca doktorska, Politechnika Krakowska 2008.
• [26] Nesterov V.N., Kislyi V.P., Timofeeva T.V., Antipina M.Yu., Semenov V.V., trans-1-Cyano-2-(2-methoxyphenyl)-1-nitroethylene, Acta Crystallographica Section C, 2000, C56, e107–e108.
• [27] Полянская А.С., Перекалин В.В., Абоскалова Н.И., Демирова З.И., Соколова Л.Н., Абдулкина З.А., Химия замещенных цианонитроалкенов II. Синтез и строение гетерилцианонитроалкенов, Журнал органической химии, 1979, 15, 2057–2061.
• [28] Troschütz R., Grün L., Synthese von basisch substituierten 5H-Pyrimido[4,5-c]-2-benzazepinen, Archiv der Pharmazie, 1993, 326, 857–864.
• [29] Абоскалова Н.И., Полянская А.С., Перекалин В.В., Демирова З.И., Соколова Л.Н., Реакция алкенилирования в присутствии кислотных катализаторов, Журнал органической химии, 1972, 8, 1332–1333.
• [30] Tamaddon F., Tayefi M., Hosseini E., Zare E., Dolomite (CaMg(CO3)2) as a recyclable natural catalyst in Henry, Knoevenagel, and Michael reactions, Journal of Molecular Catalysis A: Chemical, 2013, 366, 36–42.
• [31] Brillon D., Sauvé G., Silica Gel-Catalyzed Knoevenagel Condensation of Peptidyl Cyanomethyl Ketones with Aromatic Aldehydes and Ketones. A Novel Michael Acceptor Functionality for C-Modified Peptides: The Benzylidene and Alkylidene Cyanomethyl Ketone Function, Journal of Organic Chemistry, 1992, 57, 1838–1842.
• [32] Amantini D., Fringuelli F., Piermatti O., Pizzo F., Vaccaro L., Water, a clean, inexpensive, and re-usable reaction medium. One-pot synthesis of (E)-2-aryl-1-cyano-1-nitroethenes, Green Chemistry, 2001, 3, 229–232.
• [33] Valizadeh H., Mamaghani M., Badrian A., Effect of Microwave Irradiation on Reaction of Arylaldehyde Derivatives with Some Active Methylene Compounds in Aqueous Media, Synthetic Communications, 2005, 35, 785–790.
• [34] Bláha I., Lešetický L., Preparation and Z-E isomerization of substituted nitrostyrenes, Collection Czechoslovak Chemical Communication, 1986, 51, 1094–1099.
• [35] Shechter H., Conrad F., Daulton A. L., Kaplan R. B., Orientation in Reactions of Nitryl Chloride and Acrylic Systems, Journal of American Chemical Society, 1952, 74, 3052–3056.
• [36] Nishiwaki N., Nogami T., Tanaka C., Nakashima F., Inoue Y., Asaka N., Tohda Y., Ariga M., Aplication of Cyano-aci-Nitroacetate to Organic Synthesis. 1. Facile Synthesis of Pentanedinitrile-2,4-dinitronates, Journal of Organic Chemistry, 1999, 64, 2160–2162.
• [37] Kącka-Zych A., Domingo L.R., Ríos-Gutiérrez M., Jasiński R., Understanding the mechanism of the decomposition reaction of nitroethyl benzoate through the Molecular Electron Density Theory, Theoretical Chemistry Accounts, 2017, 136, 129.
• [38] Kącka A., Jasiński R., A dramatic change of kinetic conditions and molecular mechanism of decomposition processes of nitroalkyl carboxylates catalyzed by ethylammonium cations, Computational and Theoretical Chemistry, 2017, 1104, 37–42.
• [39] Kącka A., Jasiński R., Triethylsulfonium and triethylphosphonium cations as novel catalysts for the decomposition process of nitroethyl benzoates, Phosphorus Sulfur and Silicon and the Related Elements, 2017, 192, 1252–1258.
• [40] Kącka A., Jasiński R., DFT study of the decomposition reactions of nitroethyl benzoates catalyzed by the 1,3-dimethylimidazolium cation, Current Chemistry Letters, 2017, 6, 15–22.
• [41] Kącka A., Jasiński R., A DFT mechanistic study of thermal decomposition reactions of nitroethyl carboxylates: undermine of pericyclic insight, Heteroatom Chemistry, 2016, 27, 279–289.
• [42] Łapczuk-Krygier A., Ponikiewski Ł., Single crystal X-ray structure of (Z)-1-bromo-1-nitro-2-phenylethene, Current Chemistry Letters, 2015, 4, 21–26.

Uwagi

EN

Section "Chemistry"

PL

Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2018).