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  • 1
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocycles by Diene Synthesis, IV1). - 3-Hydroxypyrroles from Diels-Alder Adducts of Nitroso CompoundsThe methyl 2-acetoxy-4-aryl-1,3-butadiene-1-carboxylates 1 are synthesized and then allowed to react with nitrosobenzenes 2 to give mixtures of the Diels-Alder adducts 3 and 4. The isomer ratio 3 : 4 is dependent on the nature of the aryl substituents in 1 and 2; this dependence may be explained by the mechanism of the cycloaddition. - The adducts 3 are converted into 3-hydroxypyrrole-2-carboxylic acid derivatives by chromatography on silica.
    Notes: 2-Acetoxy-4-aryl-1,3-butadien-1-carbonsäure-methylester 1 werden synthetisiert und mit Nitrosobenzolen 2 zu Gemischen der isomeren Diels-Alder-Addukte 3 und 4 umgesetzt. Die Abhängigkeit des Isomerenverhältnis 3 : 4 von den Arylsubstituenten in 1 und 2 ist aus dem Mechanismus der Cycloaddition verständlich. - Die Addukte 3 lassen sich durch Chromatographie an Kieselgel in 3-Hydroxypyrrol-2-carbonsäurederivate 5 überführen.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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