The Observable Thirtyfold Degenerate Camphenehydro Cation. A Stereospecific exo-3,2-Methyl Shift and endo-6,2(exo 6,1)-Hydride Shift

Abstract

The observable camphenehydro cation 2 has been prepared and is shown to undergo two degenerate rearrangements, both well known in an indirect sense from many studies on the racemization of camphene. The results from both methods are compared and some advantages of the direct method are given; in particular it is shown that the 3,2-methyl shift is highly stereospecific. An eventual irreversible rearrangement of 2 is observed and the ion products characterized. A computer is used to systematically investigate the shortest paths from reactant to product ions.