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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 773-782 
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Selective Reactions of Hydroazulenes: Chiral Norcarane Derivatives by the Reaction of a Dihydroazulene with Singlet OxygenPhotosensitized oxygenation of the dihydroazulene 6 affords the two peroxides 7 and 8 in good overall yield. The major product is derived from the “norcaradiene” of 6. The cycloaddition with singlet oxygen occurs stereospecifically. Consecutive reaction of 7 yield chiral norcarane derivatives in stereospecific ways. Thus, by thermolysis of 7 the bisepoxide 10 is formed; reaction of 7 with triethylamine leads to the hydroxyketone 11 with MnO2 the homoquinone 13 is formed. The structures are established by spectroscopic methods.
    Notes: Die Umsetzung des Dihydroazulens 6 mit Singulettsauerstoff ergibt die beiden Peroxide 7 und 8. Das Hauptprodukt 7 leitet sich vom “Norcaradien” des Hydroazulens 6 ab. Die 1O2-Addition erfolgt stereoselektiv. Folgereaktionen von 7 ergeben chirale Norcaranderivate: Thermolyse führt zum Bisepoxid 10, mit Triethylamin entsteht das Hydroxyketon 11 und Triphenylphosphan führt unter Sauerstoffabspaltung zu den Vinyloxiranen 12a und 12b. Bei diesen Reaktionen wird jeweils nur ein Diastereomeres gebildet. Die Oxidation von 11 mit Mangandioxid ergibt das Homochinon 13. Für sämtliche Reaktionsprodukte sind spektroskopische Daten angegeben.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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