The E2C mechanism in elimination reactions. 8. Interaction of conjugating substituents with E2C- and E2H-like transition states

1976 ◽  
Vol 41 (19) ◽  
pp. 3201-3204 ◽  
Author(s):  
D. M. Muir ◽  
A. J. Parker
1963 ◽  
Vol 41 (7) ◽  
pp. 1759-1767 ◽  
Author(s):  
G. Ayrey ◽  
A. N. Bourns ◽  
V. A. Vyas

Nitrogen isotope effects have been determined for the E2 reaction of two quaternary ammonium salts with ethoxide ion in ethanol. Ethyltrimethylammonium iodide gave k14/k15 values of 1.017 at 60° and 1.015 at 95°, while 2-phenylethyltrimethylammonium bromide gave 1.012 at 40° and 1.009 at 60°. These results and the β-deuterium isotope effects reported by others have been interpreted in terms of the relative extent of Cα—N+ and Cβ—H bond weakening in the transition states of the two reactions.


1986 ◽  
Vol 39 (4) ◽  
pp. 677 ◽  
Author(s):  
J Avraamides

Transition state structures for debromination reactions of a series of para-substituted stilbene dibromides were evaluated from kinetic and product distribution data for the nucleophiles chloride, cyanide, iodide and 4-nitrothiophenoxide in dimethylformamide . The debrominations appear to utilize transition states in which nucleophilic attack is at bromine despite the strong carbon- nucleophilicity of some of the bases. Products are largely those derived from anti- debromination with all nucleophiles and reactivity is in the order 4-nitrothiophenoxide > cyanide > iodide > chloride.


2020 ◽  
Author(s):  
Deana Jaber ◽  
Maria Camarca ◽  
William Heuett

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