Evidence for the generation of p-diphenoquinodimethane

CHED 393

Darcie D. Elder and Steven P. Lorimor, lorimor@missouriwestern.edu. Department of Chemistry, Missouri Western State University, St. Joseph, MO 64507

 

p-Quinodimethanes (p-QDM) are interesting fundamental molecules and reactive, cross conjugated cyclic molecules that have been invoked as transient intermediates in a number of reactions.  p-Diphenoquinodimethane (1), a biphenyl-based reactive p-QDM, was prepared from a fluoride induced elimination of trimethylsilyl acetate from 4-[4'-((trimethylsilyl)methyl)phenyl]benzyl acetate (2).  Details of our preparation and characterization of precursor compounds, attempted observation of p-QDM 1, and oligomerization products will be presented.