Electrolysis is a technique that utilizes electric potential to oxidize or reduce compounds. It can be used to drive reactions that are normally non-spontaneous, which makes it a useful method for promoting different processes for organic compounds such as intramolecular reactions. Previous studies showed that upon electrochemical reduction of the carbon-bromine bond in methyl 2-bromomethyl benzoate, a carbanion was formed that could be expected to undergo intramolecular cyclization to give a heterocyclic compound. However, the bicyclic product would have a four-membered ring containing an excessive amount of torsional and angular strain, and thus would ultimately be too unstable to form. In this investigation, we performed multi-step synthesis to obtain ethyl 2-[2(-bromomethyl)phenoxy] acetate starting from o-cresol and investigated whether bicylic structures would form or not. Compounds were reduced by controlled-potential electrolysis in trials with and without oxygen in presence. The results showed that a number of products were generated via different intramolecular cyclization pathway.

Formation of heterocyclic compounds by electrochemically induced intramolecular cyclization

2019 Spring National Meeting

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