Activation of DMSO for Swern-type oxidation by 1,1-dichlorocycloheptatriene

作者：Thanh Vinh Nguyen^*; Hall Michael

来源：Tetrahedron Letters, 2014, 55(50): 6895-6898.

DOI：10.1016/j.tetlet.2014.10.100

• Swern oxidation
• Cycloheptatriene
• Tropylium ions
• Aromatic cations
• Alcohol oxidation

A new dimethylsulfoxide activation method employing 1,1-dichlorocycloheptatriene has been developed for a mild Swern-type oxidation of a variety of alcohols. The carbonyl products can be obtained in good to excellent yields from this operationally simple and efficient method. This work is the first report of dimethylsulfoxide activation by a simple chlorinated hydrocarbon reagent, which has the unique ability of equilibrating to its reactive aromatic cationic form.

• 出版日期2014-12-10