Synthesis of a Chlorine-Sulfonium Slide Precursor for the Study of Carbene Intermediates

Abstract

Carbenes are unique organic compounds that contain a carbon atom with a lone pair of electrons. They are extremely reactive and typically found in harsh conditions. Carbenes are often used in reactions that form carbon-carbon bonds and act as catalysts to many significant reactions in modern chemistry, but are difficult to isolate. In this research, a synthetic pathway for a carbene precursor molecule is explored. Synthesizing this molecule would allow for the study of the electronic properties and behavior of these molecules, and could provide insight into their use in the pharmaceutical industry and in forming complex molecules with interesting applications. Progress toward the synthesis of 1,3-di(2-chlorophenyl)-1,3-dione sulfonium ylide, a precursor molecule to a carbene, is presented in this work. Two of the intermediate molecules on the synthetic pathway, 2-chlorobenzoyl chloride and 1,3-di-(2-chlorophenyl)propane-1,3-dione, were successfully synthesized and characterized using GC-MS, 1H NMR, and IR spectroscopy.