Abstract

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 ether cleavage 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 cleavage are incomplete. In this work we present an alternative mechanism for ether cleavage that has implications in a number of different reactions involving boron-containing reagents.