1H NMR-based kinetic and mechanistic study of unusual skeletal rearrangements of a spirobornyl tosylate derivative

H-1 NMR analysis of the kinetics of skeletal rearrangement of optically pure 3,3-xylyl-2-exo-bornyl tosylate in CDCl3 indicates the operation of tandem autocatalytic and pseudo-first-order transformations, leading sequentially to a pair of isomeric camphene derivatives and involving partial racemization. Changing the solvent system has been shown to permit the chemoselective isolation of either of the isomeric camphenes. Copyright (C) 2010 John Wiley & Sons, Ltd.