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  • 1
    Electronic Resource
    Electronic Resource
    1,2,3,4,5,5-Hexamethyl-6-methylencyclohexa-1,3-dien und 1,2,3,4,4,5-Hexamethyl-6-methylenbicyclo[3.1.0]hex-2-en (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 1098-1103 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,2,3,4,5,5-Hexamethyl-6-methylenecyclohexa-1,3-diene and 1,2,3,4,4,5-Hexamethyl-6-methylenebicyclo[3.1.0]hex-2-eneThe title compounds 3 and 5, respectively, have been synthesized. On treatment of 3 with acids rapid isomerization to 2 takes place. Rearrangement of 5 to homofulvene 4 occurs at 60°C within 3 hours.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860613
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  • 2
    Electronic Resource
    Electronic Resource
    Umlagerungen von 2,3-Diazabicyclo[2.2.2]octanen (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 1074-1097 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Rearrangements of 2,3-Diazabicyclo[2.2.2]octane DerivativesThe ketones 4a - e have been synthesized and their reactions with methylmagnesium iodide were studied. A mechanism is given for the rearrangement of some magnesium alkoxides to 6,7-diazabicyclo[3.2.1]octane derivatives. - Dehydration of the alcohols 12d, 14a; 17a, b, g, and h with trichlorophosphane oxide is accompanied by migration of the group antiperiplanar to the hydroxy function, and thus 6,7-diazabicyclo[3.2.1]octane derivatives are formed. - Ketones 4a, c and e give on sensitized irradiation the tricyclooctane derivatives 40a, b and d, respectively, while direct irradiation leads to the bicycloheptane derivatives 42a, b and d, respectively.
    Notes: Die Darstellung der Ketone 4a - e sowie deren Umsetzung mit Methylmagnesiumiodid werden beschrieben. Für die bei einigen dieser Grignard-Additionen auftretende Umlagerung zum 6,7-Diazabicyclo[3.2.1]octan-System wird ein Mechanismus aufgestellt. - Die Dehydratisierung der Alkohole 12d, 14a, 17a, b, g und h mit Trichlorphosphanoxid erfolgt unter stereokontrollierter Umlagerung zum Bicyclo[3.2.1]octan-System mit Wanderung der zur Hydroxyfunktion antiperiplanaren Gruppierung. - Je nach Belichtungsbedingungen erhält man bei der Photoisomerisierung von 4a, c und e die Tricyclooctan-Derivate 40a, b bzw. d oder die Bicycloheptan-Derivate 42a, b bzw. d.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860612
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  • 3
    Electronic Resource
    Electronic Resource
    Halogenlactonisierung zur stereokontrollierten Synthese von rac-Isolineatin (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 61-68 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Halolactonization for a Stereocontrolled Synthesis of rac-IsolineatinThe anhydride 3 can be transformed regioselectivily into the lactones 7, 9, and the monoesters 11a, b. Under conditions of a bromolactonization 9 gives the bromohydrine 16, which can be converted into the cyclopropanecarbaldehyde 19. Salts of 11a, b react with bromine to yield the β-lactones 20a and 20b, respectivily. On treatment of 11a, b with iodine ring opening occurs, and the γ-lactones 21a and 21b, respectivily, are isolated. Iodolactonization with 22 results in the formation of 25, which provides rac-isolineatin (2).
    Notes: Das Anhydrid 3 wird von Nucleophilen regioselektiv zu 7, 9, 11a und 11b geöffnet. Unter den Bedingungen einer Bromlactonisierung liefert 9 das Bromhydrin 16, das in den Cyclopropancarbaldehyd 19 umgewandelt wird. Salze von 11a, b reagieren mit Brom zu den β-Lactonen 20a bzw. 20b. Mit Iod erfolgt die Lactonisierung erst nach konrotatorischer Öffnung von 11a, b unter Bildung der γ-Lactone 21a bzw. 21b. Der aus 3 erhaltene Ester 22 cyclisiert mit Iod zum γ-Lacton 25, das in rac-Isolineatin (2) übergeführt wird.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880112
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  • 4
    Electronic Resource
    Electronic Resource
    Reaktionen von 3,7,7-Trimethyl-4-methylenbicyclo[4.1.0]hept-2-en mit Dienophilen (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 1104-1108 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of 3,7,7-Trimethyl-4-methylenebicyclo[4.1.0]hept-2-ene with DienophilesThe preparation of the title compound 2b is described. Treatment of 2b with some dienophiles leads to the adducts 4a, b and 6b, c via ene reactions. 2b can be rearranged to give the cycloheptatriene 8.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860614
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