cis ‐Bromination of Alkynes without Cationic Intermediates | Zendy

Herges Rainer | Zendy; Papafilippopoulos Andrea | Zendy; Hess Kirsten | Zendy; Chiappe Cinzia | Zendy; Lenoir Dieter | Zendy; Detert Heiner | Zendy

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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.

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