Bradley L. Merner Auburn University Thursday, March 8, 2018 - 11:00am Chemistry Building, Room 400 Organic Seminar Our group has recently demonstrated that macrocyclic 1,4-dketones can be converted into highly strained arene-bridged systems, which represent (macrocyclic) benzenoid segments of armchair carbon nanotubes (CNTs). This non-cross-coupling-based approach enables the incorporation of strategically placed (aryl) halides that can later be engaged in programmed carbon-carbon bond forming reactions, resulting in longitudinal pi-extension of benzenoid CNT segments to polycyclic aromatic hydrocarbon (PAH) segments. The success of this approach is due to a diastereoselective Grignard reaction, which is, in turn, dependent on the size of the macrocyclic system(s) employed. Recent work that takes advantage of this size-dependent diastereoselectivity and its application to the synthesis of functionalized bent arene units, highly strained benzenoid macrocycles, and polyfunctionalized cyclobutanes will be discussed.
