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

¹H 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 © 2010 John Wiley & Sons, Ltd.