What's in a name? From designation to denunciation - The nonclassical cation controversy

Abstract

The history of the controversy and fierce debate regarding the rearrangement in chloroform of the terpene deriv., camphene hydrochloride, is discussed. The reaction belongs to a class of Wagner-Meerwein rearrangements, which are characterized by a change in the carbon-carbon bond skeleton as reactants are transformed into products. These rearrangements had long puzzled and fascinated org. chemists, since they represented a challenge to classical structural theory, which rested upon the postulate of skeletal invariance. This episode is analyzed in the context of the relationship of alternative theor. formalisms to different representations of mols. and the conflicts that arise when new forms of representation are introduced.