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  • 1
    Electronic Resource
    Electronic Resource
    Mesoionische Sechsringheterocyclen, III Reaktionen o-chinoider Verbindungen mit 6-Oxo-6H-1,3-diazin-1-ium-4-olaten (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 521-531 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Mesoionic Six-membered Heterocycles, III.  -  Reactions of o-Quinonoid Compounds with 6-Oxo-6H-1,3-diazin-1-ium-4-olatesMesoionic 6-oxo-6H-1,3-diazin-1-ium-4-olates 9 react with tetrachloro-o-benzoquinone (2, R = Cl) to give 1:1 adducts 12 which can formally be derived from ketene tautomers 13 of 9. The structure of 12f has been clarified by X-ray crystallography.
    Notes: Mesoionische 6-Oxo-6H-1,3-diazin-1-ium-4-olate 9 reagieren mit Tetrachlor-o-benzochinon (2, R = Cl) unter Bildung von 1:1-Addukten 12, die sich formal von den Ketentautomeren 13 von 9 ableiten. Die Struktur von 12f wurde durch eine Röntgenstrukturanalyse geklärt.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810317
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  • 2
    Electronic Resource
    Electronic Resource
    Mesoinische Sechsringheterocyclen, I. Synthese von 6-Oxo-6H-1,3-oxazin-3-ium-4-olaten (1978)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1978 (1978), S. 1655-1665 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Mesoionic Six-membered Heterocycles, I.  -  Synthesis of 6-Oxo-6H-1,3-oxazin-3-ium-4-olatesThe synthesis of 6-oxo-6H-1,3-oxazin-3-ium-4-olates (7) from secondary amides and malonyl dichlorides is described. It is deduced from solvolysis experiments that there is not any significant delocalisation of the positive partial charge at C-2; CNDO/2 calculations are in agreement with this assumption.
    Notes: Es wird die Synthese von 6-Oxo-6H-1,3-oxazin-3-ium-4-olaten (7) aus sekundären Säureamiden und Malonyldichloriden beschrieben. Aufgrund von Solvolyseexperimenten ist anzunehmen, daß eine signifikante Delokalisierung der positiven Partialladung an C-2 nicht erfolgt; [CNDO/2]-Rechnungen stützen diese Ansicht.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197819781012
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  • 3
    Electronic Resource
    Electronic Resource
    Reaktionen von o-Benzochinonen mit 1,3-Diarylbenzo[c]furanen (1977)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1977 (1977), S. 116-144 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of o-Benzoquinones with 1,3-Diarylbenzo[c]furanso-Benzoquinones 1, 1,2-naphthoquinone and 9,10-phenanthrenequinone react with benzo[c]-furans 2 and the fluorantheno[8,9-c]furan (7) to give the [4π + 4π] cycloadducts 3, 8, 14, 21, and the dioxoles 4, 9, 15, 22. Investigations on the systems 1f/2b and 1f/2h concerning the mechanism (solvent and temperature dependence of the distribution of the products and the rate constants) show that isopolar transition states are involved. Calculations of perturbation with the model systems 1a and benzo[c]furan are reported.
    Notes: Die o-Benzochinone 1, 1,2-Naphthochinon und 9,10-Phenanthrenchinon reagieren mit den Benzo[c]furanen 2 und dem Fluorantheno[8,9-c]furan (7) unter Bildung der [4π + 4π]-Cycloaddukte 3, 8, 14 und 21 sowie der Dioxole 4, 9, 15 und 22. Untersuchungen zum Mechanismus an den Systemen 1f/2b und 1f/2h (Lösungsmittel- und Temperaturbhängigkeit der Produktverteilung und der RG-Konstanten) zeigen, daß isopolare Übergangszustände durch-laufen werden. Über Störungsrechnungen mit den Modellsystemen 1a und Benzo[c]furan wird berichtet.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197719770114
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  • 4
    Electronic Resource
    Electronic Resource
    Diels-Alder-Reaktionen von o-Benzochinonen mit Fulvenen (1978)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1978 (1978), S. 440-472 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Diels-Alder Reactions of o-Benzoquinones with Fulveneso-Benzoquinone (1a) and alkyl-substituted o-benzoquinones 1b-d react with fulvenes 2a-d in a stereoselective and regiospecific cycloaddition to give endo-dicarbonyl compounds 3a-o and 4a, b. Photodecarbonylation and dehydrogenation of these adducts yields benzofulvenes 6, which could be synthesized from indanones 8 by an independent route.
    Notes: o-Benzochinon (1a) und alkylsubstituierte o-Benzochinone 1b-d reagieren mit Fulvenen 2a-d in einer stereoselektiv und regiospezifisch verlaufenden Cycloaddition unter Bildung von endo-Dicarbonylverbindungen 3a-o und 4a, b. Aus diesen sind durch Photodecarbonylierung und Dehydrierung Benzofulvene 6 zugänglich, die auch auf unabhängigem Wege aus Indanonen 8 dargestellt wurden.
    Additional Material: 12 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197819780310
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  • 5
    Electronic Resource
    Electronic Resource
    Cycloadditionen mit o-Benzochinon-diiminen, II. Reaktionen von o-Benzochinon-diiminen mit Olefinen (1978)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1978 (1978), S. 1129-1138 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Cycloadditions with o-Benzoquinone Diimines, II.  -  Reactions of o-Benzoquinone Diimines with OlefinsN,N'-Dibenzoyl- and N,N'-bis(phenylsulfonyl)-o-benzoquinone diimines 1 react with normal, strained and electron rich olefins in a Diels-Alder reaction with inverse electron demand to give tetrahydroquinoxalines.
    Notes: N,N'-Dibenzoyl- und N,N'-Bis(phenylsulfonyl)-o-benzochinon-diimine 1 reagieren mit normalen, gespannten und elektronenreichen Olefinen in einer Diels-Alder-Reaktion mit inversem Elektronenbedarf zu Tetrahydrochinoxalinen.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197819780712
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  • 6
    Electronic Resource
    Electronic Resource
    Reaktionen von arylsubstituierten Fulvenen mit Tetrachlor-o-benzochinon (1976)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1976 (1976), S. 793-819 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Aryl Substituted Fulvenes with Tetrachloro-o-quinones2,3,4,5-Tetraarylfulvenes 7 react with the heterodiene moiety of tetrachloro-o-benzoquinone 3 to yield the [2π + 4π] and [6π + 4π] cycloadducts 8 and 9, respectively. The structures of the [2π + 4π] adducts 8 were confirmed by oxidative degradation as well as by their synthesis from 3 with tetraarylcyclopentadienols 6 and from 3 with tetraarylcyclopentadienones (giving 10). The cisoid diene moiety in the [6π + 4π] adducts 9 could be demonstrated by Diels-Alder reaction with 4-phenyl-l,2,4-triazoline-3,5-dione (16) and/or 1,4-phthalazinedione (17). Kinetic measurements (solvent and temperature dependence) on the formation of 8 and 9 are in accord with the assumption of a multicenter cycloaddition reaction with an only moderately polar transition state. - 6,6-Diphenylfulvene gives with 3 an already known [2π + 4π] adduct of type 4 and a spirodioxole 28, the structure of which has been proved by an independent synthesis of the degradation produkt 30. The spirodioxole 28 is presumably formed from an unstable [6π + 4π] adduct of type 5.
    Notes: Bei der Addition von 2,3,4,5-Tetraarylfulvenen 7 an die Heterodieneinheit von Tetrachlor-o-benzochinon (3) werden die [2π + 4π]- und [6π + 4π]-Cycloaddukte 8 bzw. 9 erhalten. Die Strukturen der [2π + 4π]-Addukte 8 werden durch oxidativen Abbau sowie durch Synthese aus 3 mit Tetraarylcyclopentadienolen 6 und aus 3 mit Tetraarylcyclopentadienonen (zu 10) gesichert. Die cisoide Dieneinheit in den [6π + 4π]-Cycloaddukten 9 läßt sich durch Diels-Alder-Reaktion mit 4-Phenyl-1,2,4-triazolin-3,5-dion (16) und/oder 1,4-Phthalazindion (17) nachweisen. Kinetische Untersuchungen (Lösungsmittel- und Temperaturabhängigkeit) zur Bildung von 8 und 9 deuten auf eine Mehrzentrencycloaddition mit nur wenig polarem Übergangszustand hin. - 6,6-Diphenylfulven bildet mit 3 - neben einem bereits beschriebenen [2π + 4π]-Addukt des Typs 4 - ein Spirodioxol 28, dessen Struktur durch eine unabhängige Synthese des Abbauprodukts 30 bewiesen wird. Das Spirodioxol 28 entsteht wahrscheinlich aus einer instabilen [6π + 4π]-Vorstufe des Typs 5.
    Additional Material: 9 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197619760502
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  • 7
    Electronic Resource
    Electronic Resource
    Notiz zur Darstellung von 2-Methyl-3,5-diphenyl-1,2-oxazol-2-ium-4-olat (1978)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1978 (1978), S. 1540-1542 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Note on the Preparation of 2-Methyl-3,5-diphenyl-1,2-oxazol-2-ium-4-olate2-Methyl-3,5-diphenyl-1,2-oxazol-2-ium-4-olate (3) can be obtained by deprotonation of the perchlorate 2a (X = ClO4); the compound decomposes at room temperature.
    Notes: Das 2-Methyl-3,5-diphenyl-1,2-oxazol-2-ium-4-olat (3) läßt sich durch Deprotonierung des Perchlorates 2a (X = ClO4) darstellen; die Verbindung zersetzt sich bereits bei Raumtemperatur.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197819780919
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