Megan Kight

Major: Chemistry

Faculty Advisor: Richard Williams

Project Title:

A Greener Method to the Conventional  Bromination/Dehydrobromination Reactivity within Weiss-Cook Condensation Products

Abstract

The realm of this research is physical organic chemistry, a subdivision of organic chemistry, which focusses on the fundamental science governing organic molecules, their reactions, and properties. The primary goal is the synthesis and study of the first fully characterized condensed phase neutral homoaromatic compound. Homoaromaticity is a special form of aromaticity in which the through-bond interactions responsible for aromaticity are replaced by through-space interaction. Toward this end, recently, a step in our conventional reaction pathway towards a new semibullvalene analog, known as bromination, no longer produced the desired reactivity. Previously this reaction was performed using bromine, an environmentally hazardous and very toxic substance. Modifications to this process have revealed a relatively green method suitable for brominating all our systems, followed by serendipitous discovery. The newly developed reaction conditions, using NBS/DMF, also lead to dehydrobromination, the next step in our typical reaction pathway! What was previously a two-step method that used a second environmentally damaging reagent, triethylamine, is accomplished in a one-step process that substantially increases safety, improves efficiency, and reduces the chemical impact on our environment resulting from chemical waste.