- Enhanced reactivity of RC[triple bond]CZ- (R = H and Cl; Z = O, S, and Se) and the influence of leaving group on the alpha-effect in the E2 reactions.
Enhanced reactivity of RC[triple bond]CZ- (R = H and Cl; Z = O, S, and Se) and the influence of leaving group on the alpha-effect in the E2 reactions.
The Journal of organic chemistry (2010-05-21)
Xi-Guang Wei, Xiao-Ming Sun, Xiao-Peng Wu, Yi Ren, Ning-Bew Wong, Wai-Kee Li
PMID20481599
ABSTRACT
The enhanced reactivity exhibited by six pseudo-alpha-bases, RC[triple bond]CZ(-) (R = H and Cl; Z = O, S, and Se) in gas-phase E2 reactions with ethyl chloride was examined at the G2(+) level. It is found that anomalous reactivity is observed despite the fact that these chalcogen bases do not possess adjacent lone-pair electrons. The influence of the halide leaving groups on the alpha-effect and the origin of the alpha-effect in the E2 reactions of ethyl halides are investigated and discussed.