The goal of this research was to determine the scope of the newly discovered synthesis of tetrasubstituted furans via an unprecedented rearrangement. This was accomplished by synthesizing various propargylic diols and then the reaction conditions necessary to convert them to tetrasubstituted furans were determined. It was found that weaker electron donating substituents on the aromatic ring of the propargylic diol required longer heating times in order for them to be completely converted to the furan ring via the newly discovered rearrangement. A proposed mechanism for the rearrangement will be shown. Characterization of each new tetrasubstituted furan molecule was determined using nuclear magnetic resonance spectroscopy and mass spectrometry.

Novel synthesis of tetrasubstituted furan molecules

251st National Meeting (2016)

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