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Jia ZS, Rudziński J, Paneth P, et al. Borderline between E1cB and E2 mechanisms. Chlorine isotope effects in base-promoted elimination Reactions. J Org Chem. 2002;67(1):177-81doi: 10.1021/jo0159340.
Jia, Z. S., Rudziński, J., Paneth, P., & Thibblin, A. (2002). Borderline between E1cB and E2 mechanisms. Chlorine isotope effects in base-promoted elimination Reactions. The Journal of organic chemistry, 67(1), 177-81. https://doi.org/10.1021/jo0159340
Jia, Zhi Sheng, et al. "Borderline between E1cB and E2 mechanisms. Chlorine isotope effects in base-promoted elimination Reactions." The Journal of organic chemistry vol. 67,1 (2002): 177-81. doi: https://doi.org/10.1021/jo0159340
Jia ZS, Rudziński J, Paneth P, Thibblin A. Borderline between E1cB and E2 mechanisms. Chlorine isotope effects in base-promoted elimination Reactions. J Org Chem. 2002 Jan 11;67(1):177-81. doi: 10.1021/jo0159340. PMID: 11777456.
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J Org Chem. 2002 Jan 11;67(1):177-81. doi: 10.1021/jo0159340.

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

The Journal of organic chemistry

Zhi Sheng Jia, Juliusz Rudziński, Piotr Paneth, Alf Thibblin

Affiliations

  1. Institute of Chemistry, University of Uppsala, P.O. Box 531, SE-751 21 Uppsala, Sweden.

PMID: 11777456 DOI: 10.1021/jo0159340

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 degrees 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 the irreversible E1cB mechanism proposed previously (J. Am. Chem. Soc. 1977, 99, 7926) but with the E2 mechanism with transition states having large amounts of hydron transfer and very extensive cleavage of the bond to chlorine.

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