Synthetic and Computational Analysis of Possible Carbon-Oxygen and Carbon-Carbon Bond Formation in 2-(Methoxy-4-(2-phlalimidinyl)phenylsulfonyl Chloride

Ilya Deadoff and Dr. Paul Sibbald

Stetson University

Photoreactivity of 2-(methoxy-4-(2-phthalimidinyl)phenylsulfonyl chloride(MPS-Cl) was utilized as a fluorescent probe to expose different contaminants for substituted compounds of the chlorine group. Previous work by Tracy-Lynn Cleary in which MPS-Cl was found to be prone to minimal fluorescence at a certain wavelength of UV-light, however by itself MPS-Cl was and is not fluorescent. The fluorescence of MPS-Cl at a specific wavelength has provided a new scope of investigation towards identifying a potential in the variety of aromatic substitution through photodecomposition. This decomposition has been studied to find an alternative and develop a new methodology for aromatic substitutions. Through the substitution of the chlorine analog, synthetic and computation analysis yielded to explore the photodecomposition in hopes of forming new carbon-oxygen and carbon-carbon bonds through photodecomposition. Despite the lack of success in synthetically creating new carbon-oxygen and carbon-carbon bonds through photodecomposition, additional Gaussian computations offered a quantum perspective. These calculations elucidated the reasons behind the unsuccessful attempts to form these bonds and prompted further investigation. The focus shifted towards exploring the use of alternative halogen analogs and derivatives of MPS-Cl as potential starting material