2014 Scholar: Talon Kosak, MS3, Ott-Stiner Scholar
How Does BBr3 Cyclize o-alkynylanisoles to Form Benzofurans
Nature provides us with a wide array of chemicals that have beneficial uses. Cyclization reactions are important in the man-made creation of these chemicals. Past research by S3 scholar Samantha Ellis in Prof. Korich’s lab showed an unexpected cyclization reaction with o-alkynylanisoles in the presence of BBr3 instead of the expected demethylation reaction. We sought to understand this unusual reactivity using computational chemistry by comparing the energies of these competing pathways. However, we discovered that previously considered mechanisms for BBr3 assisted ether demethylation are incomplete. In this work we present an alternative mechanism for ether demethylation that has implications in a number of different reactions involving boron-containing reagents.
Faculty Mentor: Richard Lord, Chemistry