Abstract
Research project focused on the preparation of acene dinitriles from benzene 1,2-dicarbaldehyde. A Wittig reagent of fumaronitrile and triethylphosphine yielded a new C-C double. The increased the acidity of the α-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.
See full text PDF for reaction images
Faculty Sponsors
Dr. Beatrix Aukszi
Project Type
Event
Location
Alvin Sherman Library
Start Date
4-13-2012 1:00 PM
End Date
4-13-2012 5:30 PM
Total Synthesis of Functionalized Acenes
Alvin Sherman Library
Research project focused on the preparation of acene dinitriles from benzene 1,2-dicarbaldehyde. A Wittig reagent of fumaronitrile and triethylphosphine yielded a new C-C double. The increased the acidity of the α-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.
See full text PDF for reaction images
