Authors Name: 
David Jones
University College Cork
Chemical & Pharmaceutical Sciences
Award winner

Preliminary Investigation into the Optimization of Sample Systems for the Study of the Vinyl Substitution Reactions of 3(2H)-Furanones.

The 3(2H)-furanone moiety is found in a variety of natural products and molecules with bioactivity. Consequently, robust methods for the synthesis and functionalization of 3(2H)-furanones are required in order to efficiently synthesise these molecules. Currently, there are a number of methods which allow for robust and versatile functionalization of the C2 and C5 positions of the 3(2H)-furanone ring but functionalization of the C4 position is largely limited to substitution reactions involving halogens as leaving groups. There are a number of electrophilic substitutions which are known at this position but the range of known suitable substrates for vinyl nucleophilic substitutions at this position is extremely limited. Of particular interest is the incorporation of fluorine at the C4 position of the 3(2H)-furanone. Organofluorine compounds have a number of useful properties which make the study of their synthesis desirable. It has been shown that electrophilic sources of fluorine incorporate readily at the C4 position but there has been little success in incorporating fluorine via vinyl nucleophilic substitution. Theoretically, 2,2-dimethyl-4-bromo-5-(4’-bromophenyl)-3(2H)-furanone would be an ideal compound upon which to carry out vinyl nucleophilic substitutions of nucleophilic substitution. The work detailed in this report sought to examine an established synthesis of 2,2-dimethyl-4-bromo-5-(4’-bromophenyl)-3(2H)-furanone and identify opportunities for improvement of the synthetic route to this compound.