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