Borderline between E1cB and E2 mechanisms. Chlorine isotope effects in base-promoted elimination reactions

…, J Rudzinski, P Paneth, A Thibblin

Index: Jia, .Zhi Sheng; Rudzinski, Juliusz; Paneth, Piotr; Thibblin, Alf Journal of Organic Chemistry, 2002 , vol. 67, # 1 p. 177 - 181

Full Text: HTML

Citation Number: 16

Abstract

The chlorine leaving group isotope effect has been measured for the base-promoted elimination reaction of 1-(2-chloro-2-propyl) indene (1-Cl) in methanol at 30° C: k 35/k 37= 1.0086±0.0007 with methoxide as the base and k 35/k 37= 1.0101±0.0001 with triethylamine (TEA) as the base. These very large chlorine isotope effects combined with large kinetic deuterium isotope effects of 7.1 and 8.4, respectively, are consistent not with ...

Related Articles:

Borderline between E1cB and E2 mechanisms. Elimination of hydrogen chloride from fluorene derivatives

[Thibblin, Alf Journal of the American Chemical Society, 1988 , vol. 110, # 14 p. 4582 - 4586]

Enlarged deuterium isotope effects in oxyanion-catalyzed 1, 3 proton transfer competing with 1, 2 elimination as a probe of a common tightly hydrogen-bonded …

[Thibblin, Alf Journal of the American Chemical Society, 1983 , vol. 105, # 4 p. 853 - 858]

Borderline between E1cB and E2 mechanisms. Elimination of hydrogen chloride from fluorene derivatives

[Thibblin, Alf Journal of the American Chemical Society, 1988 , vol. 110, # 14 p. 4582 - 4586]

Vinylindenes and some heteroanalogues in the Diels-Alder reaction. I. Preparation of 3-vinylindene and some homologues

[Bergamasco,R.; Porter,Q.N. Australian Journal of Chemistry, 1977 , vol. 30, p. 1051 - 1059]

Protonated Benzofuran, Anthracene, Naphthalene, Benzene, Ethene, and Ethyne: Measurements and Estimates of p K a and p KR

[Thibblin, Alf Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1986 , p. 313 - 320]

More Articles...