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  • Wiley-Blackwell  (25)
  • 1985-1989  (14)
  • 1970-1974  (11)
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  • 1
    Electronic Resource
    Electronic Resource
    Vinyloge Acylverbindungen, VII. Synthese und reaktives Verhalten vinyloger N-Acyl-pyridiniumsalze (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 3470-3488 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Vinylogous Acyl Compounds, VII Synthesis and Reactive Behaviour of Vinylogous N-Acylpyridinium SaltsAddition of mineral acid salts of pyridines to propargyl aldehyde yields N-(2-formylvinyl)-pyridinium salts 7. Related N-(2-acylvinyl)-pyridinium salts 10-13 and 15 result from the reaction of β-chlorovinyl ketones with pyridine or substituted pyridines. Compounds of this type represent vinylogous N-acylpyridinium salts and are accessible to facile nucleophilic replacement of the pyridine residue: with primary and secondary aromatic amines the reaction gives N-(2-acylvinyl)-amines 21; with hydrazines, pyrazoles 22; with ammonium acetate/acetic acid, substituted pyridines 23 and bis(2-acylvinyl)-amines 24; with sodium sulfide, bis(2-acylvinyl)-sulfides 26 and 28; with carboxylates, 2-acylvinyl esters 27; and with sodium azide, 2-acylvinyl azides 29 and 30.
    Notes: Die Addition mineralsaurer Pyridinsalze an Propargylaldehyd führt zu N-[2-Formyl-vinyl]-pyridiniumsalzen 7. Entsprechende N-[2-Acyl-vinyl]-pyridiniumsalze 10-13 sowie 15 resultieren aus β-Chlor-vinylketonen und Pyridin bzw. substituierten Pyridinen. Verbindungen dieses Typs repräsentieren vinyloge N-Acyl-pyridiniumsalze und zeichnen sich durch den leichten nucleophilen Ersatz des Pyridinrestes aus: Mit primären und sekundären aromatischen Aminen reagieren sie zu N-[2-Acyl-vinyl]-aminen 21, mit Hydrazinen zu Pyrazolen 22. mit Ammoniumacetat/Eisessig zu substituierten Pyridinen 23 und Bis-[2-acyl-vinyl]-aminen 24, mit Natriumsulfid zu Bis-[2-acyl-vinyl]-sulfiden 26 bzw. 28, mit Carboxylaten zu [2-Acyl-vinyl]-estern 27 und mit Natriumazid zu [2-Acyl-vinyl]-aziden 29 bzw. 30.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701031113
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  • 2
    Electronic Resource
    Electronic Resource
    Vinyloge Acylverbindungen, IX. Zur Hydrolyse vinyloger Carbonamidiumsalze (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 210-219 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Vinylogous Acyl Compounds, IX. Hydrolysis of Vinylogous Carbonamidium SaltsThe hydrolysis of vinylogous carbonamidium salts 10 in aqueous sodium hydrogen carbonate solution does not lead - as hitherto supposed - to meso-(2-acylvinyl)acylacetaldehydes 8, but to bis(2-acylvinyl)ethers 11. The structure of these compounds results from n. m. r. and i. r. spectra and is confirmed by independent synthesis.
    Notes: Die Hydrolyse vinyloger Carbonamidiumsalze 10 in wäßriger Natriumhydrogencarbonat-Lösung führt nicht - wie bisher angenommen - zu meso-[2-Acyl-vinyl]-acylacetaldehyden 8, sondern zu Bis-[2-acyl-vinyl]-äthern 11. Die Strukturzuordnung dieser Verbindungen gründet sich auf NMR- und IR-spektroskopische Befunde sowie auf eine unabhängige synthese.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711040126
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  • 3
    Electronic Resource
    Electronic Resource
    Vinyloge Acylverbindungen, VIII. Ringöffnungsreaktionen vinyloger N-Acyl-pyridiniumsalze (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 3489-3501 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Vinylogous Acyl Compounds, VIII Ring-Opening Reactions of Vinylogous N-Acylpyridinium SaltsVinylogous N-acylpyridinium salts 2 undergo ring cleavage by alkali to azaoxonol dyes 8, which on treatment with acids reversibly release N-acylvinylated 5-aminopenta-2,4-dienals 9. Related merocyanines 11 are obtained from (pyridiniomethylene)benzocyclenone salts 10. Quarternary salts 12 derived from 3-picoline are cleaved at C-2 of the ring. Primary and secondary aromatic amines react with 9 to give pentamethincyanines 16. Treatment of 2 with aliphatic amines results in ring opening and formation of unstable azamerocyanines 22, which in part can be isolated as salts 23.  -  The spectral behaviour of the ring-fission products obtained are discussed.
    Notes: Vinyloge N-Acyl-pyridiniumsalze 2 erfahren bei Einwirkung von Alkali eine Ringauf-spaltung zu Azaoxonol-Farbstoffen 8, die mit Säuren reversibel N-acylvinylierte 5-Amino-pentadien-(2.4)-ale 9 freigeben. Entsprechende Merocyanine 11 resultieren aus [Pyridinio-methylen]-benzocyclenonsalzen 10. Vom 3-Methyl-pyridin abgeleitete Quartärsalze 12 werden am Ringatom C-2 gespalten. Primäre und sekundäre aromatische Amine überführen 9 in Pentamethincyanine 16. Aliphatische Amine öffnen 2 zu instabilen Azamerocyaninen 22, die z. T. in Form ihrer Salze 23 gefaßt werden können. - Das Spektralverhalten der erhaltenen Ringöffnungsprodukte wird diskutiert.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701031114
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  • 4
    Electronic Resource
    Electronic Resource
    Organische Phosphorverbindungen, I. Synthese und reaktives Verhalten vinyloger Phosphorsäureacylester (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 435-449 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Organic Phosphorus Compounds, I. Synthesis and Reactive Behaviour of Vinylogous Acyl Phosphates2-Acylvinyl phosphates 6 obtained from diethyl phosphorochloridate and sodium salts of 2-hydroxyvinyl ketones undergo spontaneous disproportionation to tetraethyl pyrophosphate (TEPP) 7 and bis(2-acylvinyl)ethers 8. A similar behaviour show the related diphenyl 2-acylvinyl phosphates 12, which are isolable in substance. Compounds of this type react with nucleophiles as vinylogs of acyl phosphates: primary and secondary amines lead to 2-acylvinyl amines 18, tertiary amines to vinylogous carbonamidium salts 19 and 20, J⊖ forms 2-jodovinyl ketones 21, S2⊖ bis(2-acylvinyl)sulfides 22, and SCN⊖ yields 2-(thiocyano)vinyl ketones 23. - The spectral data of the products give information about the stereochemistry of the reactions.
    Notes: Aus Phosphorsänre-diäthylester-chlorid und 2-Hydroxyvinylketon-Natriumsalzen resultierende Phosphorsäure-(2-acylvinylester) 6 unterliegen einer spontanen Disproportionierung zu Pyrophosphorsäure-tetraäthylester (TEPP) 7 und Bis(2-acylvinyl)äthern 8. Ähnlich verhalten sich die in Substanz isolierbaren Phosphorsäure-diphenylester-(2-acylvinylester) 12. Verbindungen dieses Typs reagieren mit Nucleophilen im Sinne vinyloger Phosphorsäureacylester: Primäre und sekundäre Amine führen zu (2-Acylvinyl)aminen 18, tertiäre Amine zu vinylogen Carbonamidiumsalzen 19 und 20, J⊖ liefert 2-Jodvinylketone 21, S20 Bis(2-acylvinyl)sulfide 22 und SCN⊖ 2-(Thiocyanato)vinylketone 23. - Die spektroskopischen Daten der Produkte geben Aufschluß über den sterischen Verlauf der Reaktionen.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060210
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  • 5
    Electronic Resource
    Electronic Resource
    Photochemische Umwandlungen, 64. Die 3σ → 3π-Route zu Oxepinen/Benzoloxiden (1986)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 119 (1986), S. 589-615 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Photochemical Transformations, 64. The 3σ → 3π-Route to Oxepines/Benzene OxidesThe 7-oxanorbornadiene skeleton (8a), its 2,3-bis(trifluoromethyl) derivative (8b), and several 2,3-dicarboxylic esters with potential dipolarophilic groups at C-1 (16a - d, 17a - c) were synthesized and selectively transformed into the 3-oxaquadricyclanes (18a,b, 19a - d, and 20a - c) through sensitized (8a,b) or direct (16a - d, 17a - c) photoexcitation. In the thermolysis of these oxaquadricyclanes [18a(b): Ea(C6D6) = 32.6 ± 0.3 kcal/mol (32.2 ± 1.4 kcal/mol); lg A = 15.8 (14.5)] CF3(CH3CO2) substituents at C-2(3) favor the scission of the opposite (neighbouring) cyclopropane bonds. Competition experiments with dimethyl acetylenedicarboxylate as external dipolarophile support the stepwise mechanism of the oxaquadricyclane → oxepine conversion. The intramolecular carbonyl ylide-interception cannot compete with oxepine formation in 19a - d but is efficient in 20a - c. The unusually low activation barrier (Ea(C6D6) = 23.5 ± 1 kcal/mol; lg A = 11.6) and singular specifity in case of 20a is interpreted in terms of a concerted [π2 + σ2 + σ2]-cycloaddition to the bishomofuran unit of the oxaquadricyclane skeleton.
    Notes: Das 7-Oxanorbornadien-Grundgerüst (8a), das 2,3-Bis(trifluormethyl)-Derivat (8b) und diverse 2,3-Dicarbonester mit potentiell dipolarophilen Gruppen an C-1 (16a - d, 17a - c) wurden synthetisiert und durch sensibilisierte (8a,b) bzw. direkte Lichtanregung (16a - d, 17a - c) durchweg hochselektiv in die 3-Oxaquadricyclane (18a,b, 19a - d, 20a - c) umgewandelt. Bei der Thermolyse dieser Oxaquadricyclane [18a(b): Ea(C6D6) = 32.6 ± 0.3 kcal/mol (32.2 ± 1.4 kcal/mol); lg A = 15.8 (14.5)] begünstigen CF3(CH3CO2)-Reste an C-2(3) die Spaltung der gegenüberliegenden (benachbarten) Cyclopropanbindungen. Durch Konkurrenzversuche mit Acetylendicarbonsäure-dimethylester als externem Dipolarophil wird der Mehrstufen-Mechanismus der Oxaquadricyclan → Oxepin-Isomerisierung untermauert. Die intramolekulare Carbonylylid-Abfangreaktion kann in 19a - d nicht, wohl aber in 20a - c mit der Oxepinbildung konkurrieren. Deren im Falle von 20a außergewöhnlich niedrige Aktivierungsbarriere (Ea(C6D6) = 23.5 ± 1 kcal/mol; lg A = 11.6) und singuläre Spezifität werden im Sinne einer konzertierten [π2 + σ2 + σ2]-Cycloaddition an die Bishomofuran-Einheit des Oxaquadricyclan-Gerüstes interpretiert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19861190222
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  • 6
    Electronic Resource
    Electronic Resource
    Cytotoxische Verbindungen, VI Methyl-bis-[2-chlor-äthyl]-[2-acyl-vinyl]-ammoniumsalze (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 440-447 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Cytotoxic Compounds, VI Methyl-bis-[2-chloroethyl]-[2-acylvinyl]-ammonium SaltsN-Acylvinylation of methyl-bis-[2-chloroethyl]-amine by ethynyl ketones or β-chlorovinyl ketones leads to methyl-bis-[2-chloroethyl]-[2-acylvinyl]-ammonium salts 9. The reactivity of these quarternary nitrogen mustard compounds is characterized by the rate of hydrolysis of the chloroethyl groups.
    Notes: Die N-Acylvinylierung des Methyl-bis-[2-chlor-äthyl]-amins (2) mittels Äthinylketonen oder β-Chlor-vinylketonen führt zu Methyl-bis-[2-chlor-äthyl]-[2-acyl-vinyl]-ammoniumsalzen 9. Die Reaktivität dieser quartären Stickstofflost-Verbindungen wird an der Hydrolysegeschwindigkeit der Chloräthyl-Gruppen gemessen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030214
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  • 7
    Electronic Resource
    Electronic Resource
    Pyryliumverbindungen, XXVI. Vergleichende UV/Vis-spektroskopische Untersuchungen an 3-Methyl-2,4,6-triaryl-pyrylium-perchloraten (1985)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 327 (1985), S. 151-155 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pyrylium Compounds. XXVI. Comparative U.V./Vis. Studies on 3-Methyl-2,4,6-triarylpyrylium Perchlorates
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19853270122
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  • 8
    Electronic Resource
    Electronic Resource
    Pyryliumverbindungen. 34 [1] 2-Acetonyl-2H-thiopyrane aus 2,4,6-Triaryl-thiopyryliumsalzen (1986)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 328 (1986), S. 573-581 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pyrylium Compounds. 34. 2-Acetonyl-2H-thiopyrans from 2,4,6-Triarylthiopyrylium Salts2,4,6-Triarylthiopyrylium salts 4 react with acetone in the presence of amine salts of weak acids (e.g. piperidine acetate) to give the hithero unknown 2-acetonyl-2-H-thiopyrans 5, the structure of which was established by spectroscopic methods. Depending on the nature of the amine salt used, the enamine 6 or the enol 7 of acetone may function as attacking nucleophile. Using the 2,4,6-triphenyl derivative 5a as model compound, some typical reactions of 2-acetonyl-2H-thiopyrans were studied. With 2,4-dinitrophenylhydrazine, semicarbazide and thiosemicarbazide, the carbonyl derivatives 10a-c are formed. Hydrogen peroxide in acetic acid affords the S,S-dioxide 11. Methanolic sodium methoxide or sodium hydroxide in aqueous ethanol give rise to a ring transformation yielding 1,3,5-triphenylbenzene (12) and 2,4,6-triphenylacetophenone (13). Under similar conditions, benzaldehyde reacts with 5a to give 2′, 4′, 6′-triphenylchalcone (14). Perchloric acid regenerates from 5a the initial thiopyrylium perchlorate 4a.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19863280417
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  • 9
    Electronic Resource
    Electronic Resource
    Pyryliumverbindungen. 30. C-Alkylierung von 1,3,5-Triaryl-penten-1,5-dion-Enolaten: Ein einfacher Zugang zu 3-alkylsubstituierten 2,4,6-Triaryl-pyryliumsalzen (1985)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 327 (1985), S. 983-997 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pyrylium Compounds. 30. C-Alkylation of 1,3,5-Triaryl-pentene-1,5-dione Enolates: A Simple Approach to 3-Alkylsubstituted 2,4,6-Triarylpyrylium Salts1,3,5-Triaryl-pentene-1,5-dione enolates (10), obtainable in crystalline form from 2,4,6-triarylpyrylium pseudobases (9) and sodium methoxide in benzene/ether, react in dipolar aprotonic solvents (e.g. DMSO, DMF) with various types of alkyl iodides to give C-alkylation products (11) which afford 3-substituted 2,4,6-triarylpyrylium salts (12) on treatment with perchloric acid. This reaction sequence proved to be a convenient synthetic route to pyrylium salts (12) having 3-oriented substituents such as normal or branched alkyl groups CnH2n+1 (e.g.n = 1-5), isotopically modified alkyl groups (e.g. C[2H3], C2[2H5]), allyl type substituents (e.g. CH2=CHCH2, MeCH=CHCH2, CH2, CH2=CMeCH2) or benzyl groups (e. g. PhCH2, 4-Br—C6H4CH2). Bifunctional alkylating agents (e.g. 1,4-diiodobutane, o-xylylenediiodide) resulted in a novel type of bispyrylium salts (14) with 3,3′-linkage. The pyrylium salts obtained were characterized by their 1H-n.m.r. and u.v. spectra as well as, in most cases, by transformation into the corresponding pyridine derivatives (13) and bispyridines (15) respectively.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19853270616
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  • 10
    Electronic Resource
    Electronic Resource
    Pyryliumverbindungen. XXVII. Spezifisch deuterierte Carbo- und Heterocyclen via 2,4,6-Triaryl-[3,5-2H2]pyryliumsalze (1985)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 327 (1985), S. 529-535 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pyrylium Compounds. XXVIII. Specifically Deuterated Carbo- and heterocycles via 2,4,6-Triaryl[3,5-2H2]pyrylium SaltsOn heating with catalytic amounts of bases(e.g. triethyl amine) in deuterated alcohols such as methan[2H]ol or ethan[2H]ol pseudobases of 2, 4, 6-triarylpyrylium salts 1 undergo fast1H/2H isotopic exchange reaction affording 1, 3, 5-triaryl[2, 4, 4-2H3]pent-2-ene-1,5-diones which with [2H] perchloric acid give highly deuterated 2, 4, 6-triaryl-[3, 5-2H] pyrylium perchlorates 8. These salts are obtainable also directly from 1 through a one-pot procedure by ring opening of the latter with deuterium oxide under the above-mentioned1H/2H isotopic exchange conditions followed by recyclization of the formed 1, 3, 5-triaryl[2, 4, 4-2H3]pent-2-ene-1, 5-diones with [2H]ClO4. Ring transformations of 2, 4, 6-triphenyl[3, 5-2H2]pyrylium perchlorate (8a) to 2, 4, 6-triphenyl[3, 5-2H2]nitrobenzene (9) 2, 4, 6-triphenyl[3, 5-2H2]pyridine (10), 1, 2, 4, 6-tetraphenyl[3, 5-2H2]pyrydinium perchlorate(11), 2, 4, 6-triphencyl[3, 5-2H2]thiopyrylium perchlorate(12), 2-benzoyl-3, 5-diphenyl[4-2H]furan (13), and 3, 5, 7-triphenyl-[4, 4, 6-2H3]4H-1, 2-diazepin (14) demonstrate the usability of pyrylium salts of type 8 as starting materials for syntheses of specifically deuterated carbo- and hetrocycles.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19853270402
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