Megan Kight

Major: Chemistry

Faculty Advisor: Richard Williams

Project Title:

Unusual annelated weiss cook reaction products: spectroscopic and crystallographic structural determination

Abstract

Currently, very few examples of neutral homoaromatic molecules have been synthesized and studied. We predict that a condensed phase neutral bis-homoaromatic species lies within the well-established pericyclic process, known as the Cope Rearrangement within highly strained semibullvalene analogs. The localized forms are significantly destabilized with a high degree of strain in our target systems, promoting a homoaromatic species that may exist as the ground state species. The synthetic development of synthesizing highly and often unstable molecules poses challenges and tests the boundaries in predictable chemistries. Our fundamental research extends our understanding of how and why these molecules and reactions behave the way they do. We report the ongoing physical studies into unusual outcomes from the well-established Weiss-Cook Condensation reaction in the synthetic pathway towards strained semibullvalenes. Utilizing computation combined with X-ray crystallography, efforts towards understanding the factors leading to atypical products are being investigated to understand and possibly control the reactivities observed.