Lewis acid-catalyzed rearrangement of 2,2-dichloronorbornane to 1-chloronorbornane.
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.
Smith
Kenneth
K
Department of Chemistry, University of Tennessee, Knoxville, Tennessee 37996-1600, USA.
Conley
Nicie
N
Hondrogiannis
George
G
Glover
Lyle
L
Green
James F
JF
Mamantov
Andrew
A
Pagni
Richard M
RM