
TY  - JOUR
A1  - Muir, DM 
A1  - Parker, AJ 
T1  - The E<sub>2</sub>C mechanism in elimination reactions. IX. Re-examination of the olefin-like transition-state
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1983
VL  - 36
IS  - 9
SP  - 1667
EP  - 1673
KW  - 
UR  - https://doi.org/10.1071/CH9831667 
N2  - The kinetics and product olefins arising from E2C-like elimination reactions of secondary bromides and tosylates having various alkyl and conjugating substituents at C&#945; and C&#946; are re-examined in the light of the theoretical Pross-Shaik valence-bond model and the apparent lack of a &#946;-phenyl effect. Comparison of the effect of substituents at C&#945; and C&#946; shows that whilst there are differences in reactivity and products of E2C reactions there is also a large degree of double-bond character in the transition state. There is a good correlation between the kinetics of E2C reactions and the double-bond stabilization energy arising from both alkyl and conjugating substituents. Contributing valence-bond structures, giving asymmetry and partial charge at C&#945; and C&#946; appear to vary in importance according to leaving group and substituent type. 
ER  -

