Uses
Allyl Phenyl Sulfoxide is use in: allylic sulfoxides undergo allylic rearrangement to form sulfenate esters, allowing the generation of allylic alcohols; metalated derivatives serve as ambident nucleophiles; precursors to Pummerer intermediates.
Synthesis
Oxidation of Allyl Phenyl Sulfide in dichloromethane with m-Chloroperbenzoic Acid acid (1.2 equiv) added slowly as a solution in dichloromethane at -70 °C affords the sulfoxide in high yields with minimal over-oxidation to the sulfone. The m-chlorobenzoic acid formed may be removed simply by filtration. Other oxidizing agents such as Sodium Bromite3 and Trifluoroperacetic Acid4 afford the sulfoxide in yields greater than 80% and are also highly selective.
storage
No special precautions are required. The sulfoxide may be handled normally at the bench for general weighing and transferring. However, for maximum shelf-life it is recommended that it be stored at 4 °C in a sealed vessel with exclusion of oxygen and moisture.
