19093-37-9

Allyl Phenyl Sulfoxide can undergo allylic rearrangement, bp 103-104 °C/0.36 mmHg; d 1.1205 g cm-3.

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, p. 815, 1983 DOI: 10.1055/s-1983-30526
Tetrahedron Letters, 35, p. 1413, 1994 DOI: 10.1016/S0040-4039(00)76232-0

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.

Allyl Phenyl Sulfoxide is sparingly soluble hexane; sol most other organic solvents.

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.