R. Haynes, S. Vonwiller
Apr 15, 2001
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Abstract
[19093-37-9] C9H10OS (MW 166.23) InChI = 1S/C9H10OS/c1-2-8-11(10)9-6-4-3-5-7-9/h2-7H,1,8H2 InChIKey = RLLJHMBTZSGFAS-UHFFFAOYSA-N (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) Physical Data: bp 103–104 °C/0.36 mmHg; d 1.1205 g cm−3.2 Solubility: insol water; sparingly sol hexane; sol most other organic solvents. Preparative Methods: 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. Purification: distillation in vacuo prior to use. Handling, Storage, and Precautions: 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.