Chemistry and Biochemistry
Bayer School of Natural and Environmental Sciences
Two different strategies examine intramolecular cyclizations of chiral, metalated nitriles. Cyclizations onto allylic electrophiles through competitive SN2 or SN2' displacements have different trajectories reflecting the different conformations within the forming ring. Deuterium labeling with allylic electrophiles reveals an inherent preference for SN2 displacements reflecting the optimal orbital overlap for the two different geometries.
Lu, P. (2009). Complimentary Reactivity from C- And N- Metalated Nitriles (Master's thesis, Duquesne University). Retrieved from https://dsc.duq.edu/etd/839