Lewis acid-catalyzed rearrangement of 2,2-dichloronorbornane to 1-chloronorbornane |
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| Authors: | Smith Kenneth Conley Nicie Hondrogiannis George Glover Lyle Green James F Mamantov Andrew Pagni Richard M |
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| Affiliation: | Department of Chemistry, University of Tennessee, Knoxville, Tennessee 37996-1600, USA. |
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| 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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