ChemInform Abstract: 1,2‐Derivatives of Acenaphthene. Part 7. Synthesis of Bromo Derivatives of Acenaphthylene Oxide.

Anikin, V. F.; Levandovskaya, T. I.; Stadnik, V. S.

doi:10.1002/chin.198821166

Cited by 1 publication

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“…THF, Et 2 O, dioxane), however, there is a good correlation of ln(cis/trans) values and the Kirkwood function ( Fig. 1) [15] The obtained data support the participation of tight and solvent-separated ion pairs during the process [6,7]. Non-speci®c solvents of low polarity such as hexane or carbon tetrachloride do not assist the ionization of ion pairs.…”

Section: Resultssupporting

confidence: 49%

“…Another aspect was the preparation of new cis-1,2-dibromoderivatives of substituted acenaphthenes (5c±k). It should be mentioned that cis-1,2-dibromoacenaphthene has been prepared only recently [6], whereas the trans isomer has been known for more than a century [19]. In summary, the bromination of acenaphthylenes 3a±k in dioxane leads to an appreciably high proportion of cis-dibromides (Table 2).…”

Section: Resultsmentioning

confidence: 99%

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Stereochemistry of the Addition of Bromine to Acenaphthylene Derivatives: Substituent and Solvent Effects

Anikin

Veduta

Merz

1999

Monatshefte fuer Chemie

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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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Section: Resultssupporting

confidence: 49%

Section: Resultsmentioning

confidence: 99%