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  • 1
    Electronic Resource
    Electronic Resource
    Orthoamide, XI Umsetzungen von Dimethylformamid-dialkylacetalen mit Isocyanaten (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 236-244 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XI Reactions of Dimethylformamide Dialkyl Acetals with IsocyanatesDimethylformamide dialkyl acetals react with aliphatic and aromatic isocyanates to give parabanic acid O,N-acetals (= 1,3-disubstituted 5-dimethylamino-5-alkoxy-2,4-dioxoimidazolidines) (1). It is likely that an ylide is formed as an intermediate, as shown by reactions.
    Notes: Bei der Umsetzung von Dimethylformamid-dialkylacetalen mit aliphatischen und aromatischen Isocyanaten entstehen Parabansäure-O.N-acetale (= 1.3-disubstituierte 5-Dimethylamino-5-alkoxy-2.4-dioxo-imidazolidine) (1). Die Bildung eines Ylids als Zwischenprodukt konnte wahrscheinlich gemacht werden.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030131
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  • 2
    Electronic Resource
    Electronic Resource
    Orthoamide, XIII Untersuchungen zum Reaktionsmechanismus der elektrophilen Substitution des Formyl-H-Atoms bei Orthoameisensäureamid-Derivaten (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 256-264 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XIII Studies on the Mechanism of Electrophilic Substitution of the Formyl-H Atom in Ortho Formic Acid AmidesOrtho formic acid amides and N-halogen carboxylic acid amides, halogen ureas or N-chloro urethanes primarily react to give adducts; these form ylides in the presence of bases. The ylides react by an intramolecular SE1- or SNi-mechanism to give O,N-acetals of the corresponding acyl isocyanates (isoureas).
    Notes: Bei der Umsetzung von Orthoamiden mit N-Halogen-carbonsäureamiden, -harnstoffen und N-Chlor-urethan wurden Primär-Addukte nachgewiesen. Diese bilden in Gegenwart von Basen Ylide, welche über einen intramolekularen SE1- oder SNi-Mechanismus C-N-Knüpfung eingehen unter Bildung von O.N-Acetalen der entsprechenden Acylisocyanate (Isoharnstoffe).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030133
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  • 3
    Electronic Resource
    Electronic Resource
    Orthoamide, XXIV. Synthese und Reaktionen von Amidthioacetalen und Aminalthioestern (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 3725-3731 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XXIV. Synthesis and Reactions of Amide Thioacetals and Aminal ThioestersThe amide thioacetals 2 are obtained by reaction of the N,N-dimethylformamide dimethyl sulfate adduct 1 with sodium thiolates or by treatment of N,N-dimethylformamide diethyl acetal (3) with alkanthiols. Aminal thioesters 11 are formed by reaction of tetramethylformamidinium methyl sulfate (10) with alkali alkanethiolates or by treatment of aminal-tert-butylester 12 with alkanethiols. The compounds have properties similar to those of their oxygen homologues.
    Notes: Amidthioacetale 2 erhält man aus dem N,N-Dimethylformamid-Dimethylsulfat-Addukt 1 und Natriumthiolaten oder aus N,N-Dimethylformamid-diäthylacetal (3) und Alkanthiolen, Aminalthioester 11 aus Tetramethylformamidinium-methylsulfat (10) und Alkali-alkanthiolaten oder aus dem Aminal-tert-butylester 12 und Alkanthiolen. Die Verbindungen zeigen ähnliche Eigenschaften wie ihre Sauerstoff-Homologen.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731061131
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  • 4
    Electronic Resource
    Electronic Resource
    Orthoamide, XXV. Synthese und Reaktionen von [α-(Dimethylaminomethylen)-benzyl]triphenylphosphonium-Salzen (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 3732-3742 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XXV. Synthesis and Reactions of [α-(Dimethylaminomethylene)benzyl]triphenylphosphonium SaltsBenzyltriphenylphosphonium salts (1) react with the aminal tert-butyl ester 2 to give [α-(dimethylaminomethylene)benzyl]triphenylphosphonium salts (3) or the corresponding ylenes, the benzylidenetriphenylphosphoranes (4). Hydrolysis of [α-(dimethylaminomethylene)-4-methoxybenzyl]triphenylphosphonium bromide tetrahydrate (3b · 4H2O) with aqueous potassium hydroxide results in elimination of benzene and formation of [α-(dimethylaminomethylene)-4-methoxybenzyl]diphenylphosphine oxide (8). Reaction of [α-(dimethylaminomethylene)benzyl]triphenylphosphonium bromide (3a) with sodium ethoxide affords ω-(dimethylamino)styrene (9) and triphenylphosphine oxide.
    Notes: Benzyltriphenylphosphonium-Salze (1) reagieren mit dem Aminal-tert-butylester 2 zu [α-(Dimethylaminomethylen)benzyl]triphenylphosphonium-Salzen (3) oder zu Ylenen, den Benzylidentriphenylphosphoranen (4). Die Hydrolyse von [α-(Dimethylaminomethylen)-4-methoxybenzyl]triphenylphosphonium-bromid-Tetrahydrat (3b · 4H2O) mit wäßriger Kalilauge führt unter Abspaltung von Benzol zu [α-(Dimethylaminomethylen)-4-methoxybenzyl]diphenylphosphinoxid (8). Mit Natriumäthylat entstehen aus [α-(Dimethylaminomethylen)benzyl]triphenylphosphoniumbromid (3a) ω-(Dimethylamino)styrol (9) und Triphenylphosphinoxid.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731061132
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesen in der heterocyclischen Reihe, XVIII. Synthese des Pyrimido[4,5-d]pyrimidins (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 3743-3752 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses in the Heterocyclic Series, XVIII. Synthesis of Pyrimido[4,5-d]pyrimidine4-Amino-5-pyrimidinecarbaldehyde dimethyl acetal (2a) as well as its 2-methyl (2b) and 2-phenyl derivative (2c) react with equimolar amounts of s-triazine in the heat to give the 4-(4-amino-5-pyrimidinylmethyleneamino)-5-pyrimidinecarbaldehyde dimethyl acetals 3a-c. With an excess of 5 moles of s-triazine 2a and c react after melting to yield the pyrimido[4,5-d]-pyrimidines 4a and c; under the same conditions 2b reacts to afford 4-(aminomethyleneamino)-2-methyl-5-pyrimidinecarbaldehyde (7). With an excess of 3 moles of s-triazine 2a and b react in the heat to give the 4-methoxy-3,4-dihydropyrimido[4,5-d]pyrimidines 8a and b.
    Notes: Aus molaren Mengen 4-Amino-5-pyrimidincarbaldehyd-dimethylacetal (2a) sowie dessen 2-Methyl- (2b) und 2-Phenyl-Derivat (2c) und s-Triazin entstehen in der Hitze die 4-(4-Amino-5-pyrimidinylmethylenamino)-5-pyrimidincarbaldehyd-dimethylacetale 3a-c. Mit einem 5-molaren Überschuß an s-Triazin erhält man nach einer Schmelzreaktion mit 2a und c die Pyrimido[4,5-d]pyrimidine 4a und c und mit 2b den 4-(Aminomethylenamino)-2-methyl-5-pyrimidincarbaldehyd (7). Mit einem 3-molaren s-Triazin-Überschuß entstehen in der Hitze mit 2a und b die 4-Methoxy-3,4-dihydropyrimido[4,5-d]pyrimidine 8a und b.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731061133
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  • 6
    Electronic Resource
    Electronic Resource
    Reaktionen mit Halogenwasserstoffaddukten der Nitrile, IV Zur Struktur von 6-Chlor-pyridonen-(2) (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 398-406 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions with Hydrogen Halide Adducts of Nitriles, IV The Structure of 6-Chloro-2 pyridonesThe Structure of 6-Chloro-2-pyridones in solid state and in solution is investigated by molecular weight determinations and i.r., n. m. r., and u.v.-spectra.Concentrated solutions of the pyridones in chloroform contain mainly dimers. The i.r.-spectra show that in the solid state the substances are present in the pyridone form. In solution monomeric 6-chloro-2-pyridones are in equilibrium with appreciable amounts of their hydroxy tautomers. The position of the equilibrium depends strongly on the solvent.
    Notes: Die Struktur von 6-Chlor-pyridonen-(2) wird mit Hilfe von Molekular-gewichtsbestimmungen, IR-, NMR- und UV-Spektren untersucht. Konzentrierte Lösungen der Pyridone in Chloroform enthalten vorwiegend Dimere. IR-Spektren zeigen im kristallinen Zustand die Lactamstruktur an. Monomere 6-Chlor-pyridone-(2) stehen mit 6-Chlor-2-hydroxy-pyridinen im Gleichgewicht. Die Lage des Gleichgewichts ist stark lösungsmittelabhängig.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030210
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  • 7
    Electronic Resource
    Electronic Resource
    Reaktionen mit Halogenwasserstoffaddukten der Nitrile, V Synthese von Derivaten des 3.4-Dihydro-pyridins (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 407-412 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions with Hydrogen Halide Adducts of Nitriles, V Synthesis of 3,4-Dihydropyridines6-Chloro-5-aryl-3,4-dihydro-2-pyridones (6-9) are obtained by reaction of 4-aryl-4-cyanobutyryl chlorides (1-4) with hydrogen chloride in p-dioxane. The cyclisation reactions are only possible if α-chloro-enamines can be formed as intermediates.
    Notes: 4-Aryl-4-cyan-butyrylchloride (1-4) cyclisieren in Gegenwart von Chlorwasserstoff zu 6-Chlor-5-aryl-3.4-dihydro-pyridonen-(2) (6-9). Die Ringschlußreaktion erfolgt nur dann, wenn intermediär α-Chlor-enamine gebildet werden können.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030211
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  • 8
    Electronic Resource
    Electronic Resource
    Orthoamid, XIV. Über die Umsetzung von p-Tolyl- und Anisaldehyd mit einem Aminal-tert.-butylester zu [1.2-Bis-dimethylamino-vinyl]-aryl-ketonen (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 2980-2983 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XIV. On the Reaction of p-Tolyl- and Anisaldehyde with Formic Acid Bis(dimethylaminal) tert-Butyl Ester to [1,2-Bis(dimethylamino)vinyl]-aryl Ketones (4, 5). The reaction is supposed to proceed via bis(dimethylamino)methyl aryl ketone (A, which undergoes disproportionation in a kind of Cannizzaro reaction to yield dimethylaminomethyl aryl ketone 6, isolated as an intermediate.
    Notes: Aus tert-Tolyl(1) bzw. Anisaldehyd (2) entstehen mit Bis-dimethylamino-tert-. butyloxy-methan (3) [1.2-Bis-dimethylamino-vinyl]-aryl-aryl-ketone (4, 5). Ihre Bildung wird über ein intermediäres Bis-dimethylaminomethyl-aryl-keton (A gedeutet, das in einer Art Cannizzaro-Reaktion u.a. das als Zwischenprodukt isolierte Dimethylaminomethyl-aryl-keton 6 ergibt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030935
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  • 9
    Electronic Resource
    Electronic Resource
    Orthoamide, XXVI. Synthese und Reaktionen von 1,2- Bis(dialkylamino)äthylenen (1974)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 107 (1974), S. 1545-1554 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XXVI. Synthesis and Reactions of 1,2-Bis(dialkylamino)ethylenesCH-active dimethylaminomethylene compounds react with the aminal tert-butyl ester 2 to give 1,2-bis(dimethylamino)ethylenes (3). Reanimation of 3 takes place only in the presence of an acid catalyst and only at the 2-dimethylamino group. 1-Benzoyl- (3a), 1-cyano-(3d), and 1-ethoxycarbonyl-1,2-bis(dimethylamino)ethylene (3e) undergo cyclization with amidines, guanidine, or thiourea to give the corresponding 5-dimethylaminopyrimidines (9a - f, 11) and with hydrazine to yield 4- dimethylamino-3-phenylpyrazole (10).
    Notes: CH2-aktive Dimethylaminomethylen-Verbindungen bilden mit dem Aminal-tert-butylester 2, 1,2-Bis(dimethylamino)äthylene 3. Eine Umaminierung von 3 erfolgt nur an der 2-Dimethyl-amino-Gruppe unter saurer Katalyse. 1-Benzoyl- (3a), 1-Cyan- (3d) und 1-Äthoxycarbonyl-1,2-bis(dimethylamino)äthylen (3e) reagieren mit Amidinen, Guanidin sowie Thioharnstoff unter Ringschluß zu den entsprechenden 5-Dimethylaminopyrimidinen (9a - f, 11), mit Hydrazin entsteht 4-Dimethylamino-3-phenylpyrazol (10).
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19741070515
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  • 10
    Electronic Resource
    Electronic Resource
    Orthoamide, XX. Umsetzungen von Amidacetalen und Bis-dimethylamino-methoxy-methan (Aminalester) mit Benzaziden (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 3794-3803 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Orthoamides, XX. Reactions of Amide Acetals and Bis(dimethylamino)-methoxymethane (Aminal Ester) with Benzoic AzidesUpon thermal reaction of amide acetals (1) with benzoic azides (2) only products are obtained arising from secondary reactions of the phenyl isocyanates formed intermediately from the azides. In the photochemical reaction, acyl hydrazines 15 may be isolated formed via acyl nitrene intermediates.
    Notes: Bei der thermischen Umsetzung von Amidacetalen (1) mit Benzaziden (2) werden lediglich die Folgeprodukte der intermediär aus den Aziden gebildeten Phenylisocyanate erhalten. Hingegen gelingt es bei der photochemischen Reaktion die Folgeprodukte intermediär gebildeter Acylnitrene, die Acylhydrazine 15, zu isolieren.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711041209
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