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The Rearrangement And Nucleophilic Addition Of Donor-Acceptor Cyclobutane: Novel Methodologies To Access Δ-Lactones And Ring-Opened Products, Donghyun Koo

Electronic Thesis and Dissertation Repository

Donor-acceptor (D-A) cyclobutanes are a well recognized building block in synthetic organic chemistry thanks to their unique reactivity. A variety of synthetic methodologies such as cycloaddition, rearrangement, and ring-opening addition of D-A cyclobutanes have been reported. Among them, the rearrangement reactions of D-A cyclobutanes have attracted less interest compared with other methodologies as they too often require extreme reaction conditions. To further explore the rearrangement reactions of D-A cyclobutanes, in this work a ring expansion rearrangement reaction of D-A cyclobutanes analogous to the Cloke–Wilson reaction of cyclopropanes was examined. By exploiting the solvent effect in a Brønsted acid system, we …