In the process of carrying out a simple substitution reaction, an unexpected imidazolidinone byproduct was formed. During the exploration of the formation of this byproduct, we discovered a novel mechanism for a cyclopropane ring opening. The alkyl group on the 4-position of the imidazolidinone comes from the cyclopropyl ring of cyclopropylamine. A protonation of the cyclopropane ring is proposed and supported by several experiments and other examples. Characterization of the products formed from an intermediate iminium ion as well as the proposed mechanism is discussed.<br/>

Discovery of a novel mechanism for cyclopropyl ring opening

253rd National Meeting (2017)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.