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  • 1
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ozonolysis of Enol Ethers. 9. Synthesis and Ozonolysis of 5,6,7,8-TetrahydrochromanThe regioselectivity of the transfer of three oxygens of ozone to the olefinic carbons of the rigid substituted enol ether 5,6,7,8-tetrahydrochroman (3) is proved by isolation of ω-caprinolactone 5 instead of an earlier claimed oxacyclodecanone 4.
    Additional Material: 1 Tab.
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  • 2
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Three-Oxygen-Transfer to the Olefinic Double Bond of 1,2-Diphenylacenaphthylene and of 1,2-Diphenyl-3,3,4,4-tetramethylcyclobuteneThe olefinic double bond of 1,2-diphenylacenaphthylene (1) is cleaved into its ozonide 2 (respectively into its Baeyer-Villiger rearrangement product 3) via two independent pathways: Pathway A represents the classical ozonolysis (simultaneous three-oxygen transfer) followed by a Baeyer-Villiger rearrangement, pathway B utilizes a two-step three-oxygen transfer; usual epoxidation (mono-oxygen transfer) is followed by C,C homolysis yielding a deep red diradical which shows fast two-oxygen addition (two-oxygen transfer) of molecular oxygen. The labile intermediate ozonide 2 suffers quantitative Baeyer-Villiger rearrangement under reaction conditions necessary to achieve oxirane C,C-cleavage. Therefore, the particularly stable ozonide 11 from 1,2-diphenyl-3,3,4,4-tetramethylcyclobutene (10) is prepared according to pathway B starting from Arnolds's oxirane 12. Both oxidation methods are compared with regard to ozonide formations from olefins.
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  • 3
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Details on Ozonolyses of Substituted Cyclopentenes
    Additional Material: 1 Tab.
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 710 (1967), S. 137-160 
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Die Herstellung von Dihydropyrogallol (47) aus Δ1-Cyclohexenon wird eingehend beschrieben. Auf dem gleichen Wege werden aus Acrolein das Trioseredukton (9) und aus Crotonaldehyd das Methylredukton (15) erhalten. Von besonderem Interesse sind die hohe Reinheit und Luftbeständigkeit der hergestellten Präparate. Phenylredukton (23) und Indanoredukton (27b) konnten infolge ihrer Instabilität nur durch Reaktionen nachgewiesen und als Derivate gefaßt werden.
    Additional Material: 2 Tab.
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  • 5
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Catalyzed Insertion Reactions into Alcoholic OH-Groups by Diazo Derivatives of Compounds with Activated Methylene GroupsA preparatively facile method is described for decomposing the diazo compounds 6, 9, and 12, which are prepared from the carbonyl- and sulfonyl-activated methylene compounds 5, 8, and 11 in aliphatic alcohols with OH-insertion. The yields of insertion products 7, 10, and 13 becomes greater and greater compared with those of the products of a preceding Wolff rearrangement the less the carbeniate electron pair of the diazo compound is delocalized as a consequence of mesomerism. cr-Methoxy β-diketones 13 are therefore better prepared by an improved ester condensation.
    Notes: Für die Zersetzung der Diazoverbindungen 6, 9 und 12, die aus den carbonyl- und sulfonylaktivierten Methylenverbindungen 5, 8 und 11 erhalten werden, in aliphatischen Alkoholen unter OH-Insertion wird eine präparativ einfache Methode beschrieben. Die Ausbeuten an Insertionsprodukten 7, 10 und 13 dominieren um so mehr über die an Folgeprodukten einer Wolff-Umlagerung, je weniger das Carbeniat-Elektronenpaar der Diazoverbindung infolge Mesomerie delokalisiert ist. Die cr-Methoxy-β-diketone 13 werden deshalb günstiger über eine verbesserte Esterkondensation hergestellt.
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  • 6
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Stabilization Reactions at Trisubstituted Arylazomethanes, I. - Isomerization of Arylazo Coupling Products of u-Acylated u-Sulfonyl Ethers and Corresponding ThioethersArylazo coupling products 4 of cr-methoxy cr-sulfonyl ketones (and corresponding thioethers 11) undergo facile isomerizations on heating in inert solvents. Sulfonamides 6 result as products of a formal 1,3-shift of the sulfonyl substituent; simultaneously, cis-hydrazones cis-7 are generated as products of a 1,5-shift of the sulfonyl group and are isomerized in turn to the thermodynamically more stable trans-hydrazones trans-7 at slightly elevated temperatures.
    Notes: Arylazokupplungsprodukte 4 von cr-Methoxy-α-sulfonylketonen (und entsprechender Thioäther 11) erleiden beim Erwärmen in inerten Lösungsmitteln leicht Isomerisierungen. Als Folgeprodukte einer formalen 1,3-Verschiebung des Sulfonylrestes treten dabei die Sulfonamide 6 auf; gleichzeitig werden als Produkte einer 1,5-Verschiebung des Sulfonylrestes die cis-Hydrazone cis-7 gebildet, die bei etwas erhöhter Temperatur zu den thermodynamisch stabileren trans-Hydrazonen trans-7 weiterisomerisiert werden.
    Additional Material: 3 Tab.
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  • 7
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1477-1481 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: α-Oxosulfones, 3.  -  Reactions of Acyclic α-OxosulfonesThe course of reactions of acyclic α-oxosulfones with protic and aprotic nucleophiles is described. A far-reaching analogy to reactions of acyl halides is noticed.
    Notes: Die Reaktionsweise von acyclischen α-Oxosulfonen mit protischen und aprotischen Nucleophilen wird beschrieben. Dabei wird eine weitgehende Analogie zu Reaktionen von Acylhalogeniden festgestellt.
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  • 8
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1739-1743 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: α-Oxosulfones, 5. - reactions of a Cyclic α-Ketosulfone5,5-Dioxo-6H-dibenzo[b,d]thiopyran-6-one (4) as the first „real α-ketosulfone“ was isolated, and some of its reactions were studied. Apparently, 4 represents formally a border case between a thioester S,S-dioxide and an „α-ketosulfone“.
    Notes: Als erstes „wirkliches α-Ketosulfon“ wurde 5,5-Dioxo-6H-dibenzo[b,d]-thiopyran-6-on (4) isoliert. Beim Studium einiger seiner Reaktionen zeigte sich, daß 4 formal einen Grenzfall zwischen einem Carbonsäurethioester-S,S-dioxid und einem „α-Ketosulfon“ darstellt.
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  • 9
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 716 (1968), S. 87-97 
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Die Herstellung von α-Alkoxy-β-ketosulfonen 6 aus α-Brom-α-alkoxy-methylketonen 4 und einige ihrer Reaktionen werden beschrieben. In alkalischer Lösung bilden die Sulfone 6 die Anionen von Sulfonylredukton-2-alkyläthern.
    Additional Material: 3 Tab.
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  • 10
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 723 (1969), S. 205-207 
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of a Free α-Diazo Carboxylic AcidThe synthesis of the stable α-diazo carboxylic acid 4, its properties and reactions are described.
    Notes: Die Darstellung der stabilen α-Diazocarbonsäure 4 sowie deren Eigenschaften und Reaktionen werden beschrieben.
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