Lewis Acid-Catalyzed Rearrangement of 2,2-Dichloronorbornane to 1-Chloronorbornane
Publication type: Journal Article
Publication date: 2004-05-29
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
15230613
Organic Chemistry
Abstract
The mechanism for the unusual AlCl(3)-catalyzed rearrangement of 2,2-dichloronorbornane to 1-chloronorbornane in pentane has been elucidated; the reaction, which also yields four isomeric dichloronorbornanes, occurs in three steps: (1). ionization to form the 2-chloro-2-norbornyl cation, which was fully characterized by two-dimensional (1)H and (13)C NMR in SbF(5)/SO(2)ClF; (2). Wagner-Meerwein shift to yield the 1-chloro-2-norbornyl cation, which was partially characterized by (1)H NMR; and (3). hydride abstraction.
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Smith K. et al. Lewis Acid-Catalyzed Rearrangement of 2,2-Dichloronorbornane to 1-Chloronorbornane // Journal of Organic Chemistry. 2004. Vol. 69. No. 14. pp. 4843-4844.
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Smith K., Conley N., Hondrogiannis G., Glover L., Green J. F., Mamantov A., Pagni R. M. Lewis Acid-Catalyzed Rearrangement of 2,2-Dichloronorbornane to 1-Chloronorbornane // Journal of Organic Chemistry. 2004. Vol. 69. No. 14. pp. 4843-4844.
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TY - JOUR
DO - 10.1021/jo030350e
UR - https://doi.org/10.1021/jo030350e
TI - Lewis Acid-Catalyzed Rearrangement of 2,2-Dichloronorbornane to 1-Chloronorbornane
T2 - Journal of Organic Chemistry
AU - Smith, Kenneth
AU - Conley, Nicie
AU - Hondrogiannis, George
AU - Glover, Lyle
AU - Green, James F.
AU - Mamantov, Andrew
AU - Pagni, Richard M.
PY - 2004
DA - 2004/05/29
PB - American Chemical Society (ACS)
SP - 4843-4844
IS - 14
VL - 69
PMID - 15230613
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2004_Smith,
author = {Kenneth Smith and Nicie Conley and George Hondrogiannis and Lyle Glover and James F. Green and Andrew Mamantov and Richard M. Pagni},
title = {Lewis Acid-Catalyzed Rearrangement of 2,2-Dichloronorbornane to 1-Chloronorbornane},
journal = {Journal of Organic Chemistry},
year = {2004},
volume = {69},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/jo030350e},
number = {14},
pages = {4843--4844},
doi = {10.1021/jo030350e}
}
Cite this
MLA
Copy
Smith, Kenneth, et al. “Lewis Acid-Catalyzed Rearrangement of 2,2-Dichloronorbornane to 1-Chloronorbornane.” Journal of Organic Chemistry, vol. 69, no. 14, May. 2004, pp. 4843-4844. https://doi.org/10.1021/jo030350e.