Stereochemistry of the addition of bromine to acenaphthylene derivatives: Substituent and solvent effects

Anikin, Valeriy F. and Veduta, Vera V. and Merz, Andreas (1999) Stereochemistry of the addition of bromine to acenaphthylene derivatives: Substituent and solvent effects. MONATSHEFTE FUR CHEMIE, 130 (5). pp. 681-690. ISSN 0026-9247,

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Abstract

Addition of bromine to acenaphthylene and 5-bromoacenaphthylene in aprotic solvents of different polarity is not stereospecific: 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 first time.

Item Type: Article
Uncontrolled Keywords: BROMONIUM; PRODUCT; ION; acenaphthene derivatives; electrophilic addition; stereoselectivity; solvent effects
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie
Depositing User: Dr. Gernot Deinzer
Date Deposited: 25 Oct 2022 12:54
Last Modified: 25 Oct 2022 12:54
URI: https://pred.uni-regensburg.de/id/eprint/48298

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