Using conformational landscape to explain the non-classical nature of cyclobutyl and cyclopropylcarbinyl cations

Abstract

Carbocations, organic chemistry corner stones, play a major role in carbonic skeletal rearrangements. A turning point in their study was the introduction of non-classical Carbocations, which establish a rapid equilibrium among their different forms to distribute their positive charge. Here a new stereospecific mechanistic pathway for cyclopropylcarbinyl and cyclobutyl cations is proposed. Carbon scrambling is plotted into a conformational landscape model, usually used for true conformers. A deeper insight into these cationic interconversions provides the underpinning principals that govern their dynamics. Future studies are expected to reveal the role of cyclopropyl structural motifs in the vast arrays of natural products and their dynamics.