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cis ‐Bromination of Alkynes without Cationic Intermediates
Author(s) -
Herges Rainer,
Papafilippopoulos Andrea,
Hess Kirsten,
Chiappe Cinzia,
Lenoir Dieter,
Detert Heiner
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461632
Subject(s) - halogenation , tribromide , cationic polymerization , chemistry , selectivity , mechanism (biology) , adduct , organic chemistry , computational chemistry , medicinal chemistry , philosophy , catalysis , epistemology
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.