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Base‐Promoted 1,4‐Elimination Reactions: On the Origin of an Eventual syn ‐Stereoselectivity
Author(s) -
Schlosser Manfred,
Tarchini Claudio,
An Tran Dinh,
Ruzziconi Renzo,
Bauer Paul J.
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198110411
Subject(s) - stereoselectivity , chemistry , elimination reaction , polar , solvent , base (topology) , concerted reaction , reaction mechanism , mechanism (biology) , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , catalysis , physics , mathematical analysis , quantum mechanics , mathematics , astronomy
A “conveyor” or a concerted, E1cb‐like mechanism is involved in the 1,4‐elimination of HCl from E‐(1) and Z‐(1). The particular mechanism depends on the solvent: In polar solvents the concerted process is effective, in non‐polar solvents the “conveyor” process. Due to the larger distance between the reaction centers in polar solvents alkyne‐forming 1,4‐eliminations are less stereoselective than analogous 1,2‐elimininations.