Addition of bromine to acenaphthylene and 5-bromoacenaphthylene in aprotic solvents of different polarity is not stereospeci®c: both trans and cis isomers of the corresponding 1,2-dibromides are formed. In general, the relative proportion of syn addition increases with decreasing solvent polarity; the highest percentage of cis products is observed in 1,4-dioxane. The stereochemistry of bromine addition to nine additional 3-, 5-, and 5,6-substituted acenaphthylenes in dioxane is reported. A number of new cis-1,2-dibromoacenaphthenes have been isolated for the ®rst time.
Stereochemie der Addition von Brom an Derivate des Acenaphthylens: Ein¯u È sse von Substituenten und Lo ÈsungsmittelnZusammenfassung. Die Addition von Brom an Acenaphthylen und 5-Bromacenaphthylen erfolgt in aprotischen Lo Èsungsmitteln unterschiedlicher Polarita Èt unspezi®sch: sowohl cis-als auch transProdukte werden gebildet. Allgemein steigt der Anteil der syn-Addition mit steigender Polarita Èt des Lo Èsungsmittels, wobei der sta Èrkste Effekt bei 1,4-Dioxan beobachtet wird. Die Stereochemie der Bromaddition an neun weitere 3-, 5-und 5,6-Acenaphthylenderivate wird beschrieben; einige cis-1,2-Dibromacenaphthenderivate wurden erstmals erhalten.
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