In conclusion, we have undertaken a comprehensive study of sulfinate protecting group stability by subjecting six different sulfinate protecting groups to a variety of common synthetic transformations. Additionally, methods to synthesize aryl containing SPGs were also assessed. From these studies, it was found that 2trimethylsilylsulfone (SES) and the newly disclosed ortho-nitrobenzyl Rongalite sulfone (oNB-R) possessed a broad stability profile, a facile method of synthesis, and a selective and orthogonal deprotection/fluorination procedure. An additional SPG, paramethoxybenzyl Rongalite was also found to have broad stability and an intriguing deprotection/fluorination condition of selectfluor and light. Ultimately, the SPG chosen in a synthetic endeavor should be tailored to the synthetic conditions used and the functionality present. The studies above outline the benefits and drawbacks of each SPG while providing additional groups with novel, orthogonal deprotection conditions. Overall, these groups should allow for more structural diversity in the synthesis of SF containing small molecule inhibitors or probes.