Display options
Cite
Walker GE, Kronja O, Saunders M. Isotopic scrambling in Di-13C-labeled 2-butyl cation: evidence for a protonated cyclopropane intermediate. J Org Chem. 2004;69(10):3598-601doi: 10.1021/jo049951b.
Walker, G. E., Kronja, O., & Saunders, M. (2004). Isotopic scrambling in Di-13C-labeled 2-butyl cation: evidence for a protonated cyclopropane intermediate. The Journal of organic chemistry, 69(10), 3598-601. https://doi.org/10.1021/jo049951b
Walker, Gary E, et al. "Isotopic scrambling in Di-13C-labeled 2-butyl cation: evidence for a protonated cyclopropane intermediate." The Journal of organic chemistry vol. 69,10 (2004): 3598-601. doi: https://doi.org/10.1021/jo049951b
Walker GE, Kronja O, Saunders M. Isotopic scrambling in Di-13C-labeled 2-butyl cation: evidence for a protonated cyclopropane intermediate. J Org Chem. 2004 May 14;69(10):3598-601. doi: 10.1021/jo049951b. PMID: 15132583.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2004 May 14;69(10):3598-601. doi: 10.1021/jo049951b.

Isotopic scrambling in Di-13C-labeled 2-butyl cation: evidence for a protonated cyclopropane intermediate.

The Journal of organic chemistry

Gary E Walker, Olga Kronja, Martin Saunders

Affiliations

  1. Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.

PMID: 15132583 DOI: 10.1021/jo049951b

Abstract

The (13)C NMR spectrum of 2-butyl-1,2-(13)C(2) cation (1) is unchanged on heating the sample to -78 degrees C, indicating no isomerization to another isotopomer. In contrast, the spectrum of 2-butyl-2,3-(13)C(2) cation (2) shows rapid formation of all of the other isotopomers except 1. These results are consistent with a protonated cyclopropane intermediate in the rearrangement process. In this mechanism, either C(1) and C(2) or C(3) and C(4) interchange. Only the bond between C(2) and C(3) breaks.

Publication Types