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The Mechanism of Bimolecular β‐Elimination Reactions
Author(s) -
Bunnett J. F.
Publication year - 1962
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.196202251
Subject(s) - mechanism (biology) , chemistry , elimination reaction , linkage (software) , bond , computational chemistry , state (computer science) , reaction mechanism , orientation (vector space) , catalysis , computer science , physics , medicinal chemistry , economics , organic chemistry , mathematics , quantum mechanics , algorithm , geometry , biochemistry , finance , gene
In bimolecular β‐elimination (E 2 mechanism), several bonds are ruptured or formed in one concerted reaction step. However, the various aspects of bond‐making or ‐breaking need not be completely synchronous. In the E 2 transition state for elimination HX, rupture of the CX bond may be more advanced than that of the CH linkage, or vice versa. Factors influencing the relative extents of rupture of these two bonds at the transition state are discussed, and the consequences of non‐synchroneity in one sense or the other are developed from theory and illustrated from experiment. This treatment provides an understanding of the Hofmann‐vs.‐Saytzeff orientation problem.