With a mild method to access iodo-BCPs 2a-c in hand, we were intrigued by C-N bond functionalizations based on the results of Adcock and Wiberg (Scheme 2A-B). We hypothesized that we could potentially form amino-substituted BCP products when 2b is treated with an amine in a polar aprotic solvent. Alternatively, if the rearrangement described by Wiberg 14, 24A occurred, we could expect a substituted BCB product. The 1 H NMR and C HSQC spectrum of 3 displayed two singlets corresponding to a pair of magnetically inequivalent protons attached to the same carbon, suggesting the BCB was the product. To confirm, an X-ray crystal structure of 3 was acquired that proved a rearrangement had occurred to the BCB.