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    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Polyhalogenated Bicyclo[4.2.0]octa-1,5,7-trienes, VI1). -Cyclodimerization of 2-Bromo-1,1,4-trichloro-1-buten-3-yne and 1,1,4-Trichloro-2-methyl-1-buten-3-yneThermal dimerization of the butenynes 1c, d to the bicyclo[4.2.0]octa-1,5,7-trienen 3c,d (α-dimers) and further rearrangements of these compounds into the benzocyclobutenes 2c,d (β0dimers) and cyclooctatetraenes 8a,b (γ-dimers) are described. The methyl substituted α-dimer 3d aromatizes much more easily to the β-dimer than the analogous perhalogenated systems 3a-c. The position of the methyl groups in 3d is proved by hydrolysis of 2d to 7b and oxidation to 9b. Compound 3c was converted into the benzonitrile 4 by ammonia.
    Notes: Die thermische Dimerisierung der Butenine 1c,d zu den Bicyclo[4.2.0]octa-1,5,7-trienen 3c,d (α-Dimere) wird beschrieben. Die Verbindungen lagern sich weiter in die Benzocyclobutene 2c,d (β-Dimere) und in die Cyclooctatetraene 8a, b (γ-Dimere) um. Die Methylgruppen in 3d, deren Stellung durch Hydrolyse von 2d zu 7b und weitere Oxidation zu 9b bewiesen wird, setzen die thermische Stabilität stark herab. Verbindung 3d aromatisiert viel leichter zum β-Dimeren als ihre perhalogenierten Analogen 3a-c. die Ammoniakreaktion von 3c führt zum Benzonitril 4.
    Type of Medium: Electronic Resource
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