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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: Polyhalogenated Bicyclo[4.2.0]octa-1,5,7-trienes, II.  -  Cyclodimerization of 1,1,2-Trichloro-4-bromo-1-butene-3-yneThe course of cyclodimerization of the title compound 1 is the same as that with perchlorobutenyne. The obtained bicyclic α-dimer 2 rearranges in dipolar aprotic solvents at 20° into the benzocyclobutene 4 (β-dimer) and in formic acid at 20° into the cyclooctatetraene 8 (γ-dimer). The position of the bromine atoms in the four-membered ring of 2 and 4, confirmed by the degradation products 3, 6 and 7, agrees with the postulated mechanism of cyclodimerization. 8 and perchlorocyclooctatetraene are converted by sodium methylate into the tetramethoxy-substituted benzocyclobutene 10.
    Notes: Die Cyclodimerisierung der Titelverbindung 1 verläuft analog derjenigen des Perchlorbutenins zum Bicyclus 2 (α-Dimeres), das sich in dipolar-aprotischen Lösungsmitteln bei 20° in das Benzocyclobuten 4 (β-Dimeres) und mit Ameisensäure bei 20° in das Cyclooctatetraen 8 (γ-Dimeres) umlagert. Die Stellung der Bromatome am Vierring von 2 und 4, die aus der Konstitution der Abbauprodukte 3, 6 und 7 hervorgeht, steht im Einklang mit dem postulierten Mechanismus der Dimerisation von 1. 8 und Perchlorcyclooctatetraen geben mit Natriummethylat das Tetramethoxybenzocyclobuten 10.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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