The Role of the Leaving Group in the Photo-Favorskii Rearrangement of P-hydroxyphenacyl

The p-hydroxyphenacyl group has several features that make it an attractive photoremovable protecting group. Literature examples support this statement and the benzoate, formate, and sulfonate derivatives are not exceptions. The synthesis of these targets is straight forward involving few synthetic steps that produce the desired product in good to excellent yield. The purification of these targets is simplified by the fact that these derivatives are all solids. Their solubility and stability in polar organic solvents and in water at low concentrations, the formate solubility in water is the exception, make them ideal for use in organic synthesis and in biological applications.