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  • 1
    Electronic Resource
    Electronic Resource
    Cyclopropan-Derivate, 2. Selbst-Acylierung der α-Alkyl-γ-lactone zu Herstellung von Bis(1-alkylcyclopropyl)ketonen über Spiro[4.4]acetale (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 2161-2166 
    Details
    ISSN: 0009-2940
    Keywords: Acetals ; Ketones ; γ-Lactones ; Butanolides ; Spiro compounds ; Cyclopropyl compounds ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cyclopropane Derivatives, 2.  -  Self-Acylation of α-Alkyl-γ-lactones To Give Bis(1-alkylcyclopropyl)ketones via Spiro[4.4]acetalsHigh-yield synthetic ways are recommended for the title lactones 1.The coupling of two 2-alkyl-4-butanolides is possible in an inter-(1b, c) or intramolecular fashion (4c) to give spiro[4.4] acetals 8 or 9 respectively, in the absence of hindering substituents. Symmetrically substituted bis(1-alkylcyclopropyl)ketones 12 and 13 may be prepared by acidic cleavage of those spiro[4.4] acetals lacking 2,7-substituent.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901231112
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  • 2
    Electronic Resource
    Electronic Resource
    Cyclopropan-Derivate, 3. (1-Alkylcyclopropyl)ketone durch Acylierung von α-substituierten γ-Lactonen (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 2167-2172 
    Details
    ISSN: 0009-2940
    Keywords: Acylation ; Ketones ; γ-Lactones ; Butanolides ; Cyclopropyl compounds ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cyclopropane Derivatives, 3.  -  (1-Alkylcyclopropyl)ketones by Acylation of α-Substituted γ-LactonesThe 2-acylation of 2-substituted 4-butanolides 2 is moderately sensitive to steric crowding, whereas the subsequent ring- opening of 2-acyl-2-alkyl-4-butanolides 4, 11 to give-chloro ketones 6, 12 by chloride-transferring acid derivatives be-comes difficult with bigger lactone substituents. Similar observations pertain to the preparation of y-chlorobutanoyl chlorides 10 from 2-alkyl-4-butanolides 2. The proper choice of the starting 4-butanolides (2a, b or 14 but not 2c) provides for an indirect coupling of two different lactones to y,y-dichloro ke-tones 12. Dicyclopropyl ketones 13 with variable patterns of substitution may thus be prepared from 4-butanolides in a direct manner with global yields exceeding 50% and without purification of intermediate products (except for acid chlorides like 10).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901231113
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