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

被引:32
作者
Thanh Vinh Nguyen [1 ]
Hall, Michael [1 ]
机构
[1] Curtin Univ, Dept Chem, Perth, WA 6102, Australia
关键词
Swern oxidation; Cycloheptatriene; Tropylium ions; Aromatic cations; Alcohol oxidation; ALCOHOLS;
D O I
10.1016/j.tetlet.2014.10.100
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6895 / 6898
页数:4
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