cis-Bromination of Alkynes without Cationic Intermediates

cis-Bromination of Alkynes without Cationic Intermediates

Surprising insight into a classical mechanism is provided by theoretical and experimental investigations on the bromination of alkynes. In nonpolar solvents the bromination of acetylene via a covalent tribromide adduct is strongly favored over the textbook mechanism via a bridged bromirenium ion. Th...

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Veröffentlicht in:Angewandte Chemie International Edition 2005-02, Vol.44 (9), p.1412-1416
Hauptverfasser: Herges, Rainer, Papafilippopoulos, Andrea, Hess, Kirsten, Chiappe, Cinzia, Lenoir, Dieter, Detert, Heiner
Format: Artikel
Sprache:eng
Schlagworte:
Acetylene - chemistry
alkynes
Alkynes - chemistry
bromination
Bromine - chemistry
Bromine Compounds - chemical synthesis
Bromine Compounds - chemistry
density functional calculations
electrophilic addition
Hydrocarbons, Halogenated - chemical synthesis
Hydrocarbons, Halogenated - chemistry
Isomerism
Models, Chemical
Molecular Structure
reaction mechanisms
Solvents - chemistry
Static Electricity
Thermodynamics
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Beschreibung
Zusammenfassung:Surprising insight into a classical mechanism is provided by theoretical and experimental investigations on the bromination of alkynes. In nonpolar solvents the bromination of acetylene via a covalent tribromide adduct is strongly favored over the textbook mechanism via a bridged bromirenium ion. The structurally interesting intermediate explains the syn selectivity of the bromination of strained cycloalkynes.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200461632