Student Author(s)

Jessica Scott

Faculty Mentor(s)

Dr. Jason Gillmore

Document Type


Event Date



Our computational studies predict that replacing the methyl groups in our previous generation dimethylquinazolinespirohexadienone (QSHD) photochrome will make for a much more potent photochromic photooxidant. A previous group member determined that it is not possible to carry out the synthesis with trifluormethyl groups present from the start as they completely inhibit a key nitration step. Meanwhile a current labmate has devised a synthesis of dihaloQSHD that could be amenable to installing the trifluoromethyls at a variety of points along the synthetic route. Five different options of when to perform this transformation are possible, replacing either a bromide or an iodide. I have undertaken model studies on four different aryl bromides and iodides to optimize trifluoromethylation conditions. The effects of competing reactions and inhibitors were studied through competition experiments. Together these allow us to identify the most promising targets for trifluoromethylation in the synthesis of the desired bis(trifluoromethyl)QSHD.


This work was supported by the National Science Foundation under Career Grant CHE- 0952768, by the Camille & Henry Dreyfus Foundation by a Henry Dreyfus Teacher- Scholar award, and by a Schaap Research Fellowship from Hope College.