Total Synthesis of Functionalized Acenes

Total Synthesis of Functionalized Acenes

This research project is focused on the total synthesis of three different acene dinitriles. With the understanding that syntheses of such acenes are affected by chemoselectivity, it is imperative that proper protocol be followed in order to produce the desired acenes in a favorable and useful yield. By means of Wittig reactions, condensation and reduction reactions the final product will be formed. Acene-2,3- dicarbaldehyde is utilized as a starting compound undergoing a Witting reaction and a consecutive Aldol reaction to produce a second ring with diester functionalities. Following reduction to a dialdehyde a modified Wittig reaction and consecutive Aldol reaction will ensure formation of the third fused ring with dinitrile functionalities. Formation of proper intermediates and final product will be confirmed via Infrared Spectroscopy (IR), Gas Chromatography-Mass Spectrometry (GC-MS), and Thin Layer Chromatography (TLC). Obtained products will be utilized for further research by collaborator, Dr. Donald Baird.