Total Synthesis of Functionalized Acenes
Research project focused on preparation of acene dinitriles from benzene 1,2-dicarbaldehyde. A Wittig reagent of fumaronitrile and triethylphosphine yielded a new C-C double. The increased acidity of the a-H, between the new alkene bond and a cyano group, allowed an Aldol reaction to take place and resulted in a ring closure. Condensation reaction established aromaticity in the new ring, carrying dicyano functionality. To allow additional ring formations via reaction sequence repetitions, nitrile groups were reduced with DIBALH to dialdehydes.
Parikh, Reena; Aukszi, Beatrix; and Baird, Donald, "Total Synthesis of Functionalized Acenes" (2012). Chemistry and Physics Faculty Proceedings, Presentations, Speeches, Lectures. 102.