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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 10
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Original Articles

Efficient and mild swern oxidation using a new sulfoxide and bis(trichloromethyl)carbonate

Xiaojing YeCollaborative Innovation Center of Green Pharmaceutical Engineering, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, China
,
Hongliang FuCollaborative Innovation Center of Green Pharmaceutical Engineering, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, China
,
Jiahao MaCollaborative Innovation Center of Green Pharmaceutical Engineering, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, China
&
Weihui ZhongCollaborative Innovation Center of Green Pharmaceutical Engineering, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, ChinaCorrespondence[email protected]
Pages 885-892 | Received 14 Oct 2015, Published online: 31 May 2016
 
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ABSTRACT

A new type of sulfoxide, 4-(2-(2-(methylsulfinyl) ethyl)-4-nitrophenyl)- morpholine (I), was designed and prepared in good yield. Upon the combination of I and bis(trichloromethyl)carbonate, the Swern oxidation of primary and secondary alcohols was significantly promoted under mild conditions, which afforded the corresponding aldehydes or ketones in good yields. It is noteworthy that the reoxidation of the isolated by-product sulfide V could be further recycled in Swern oxidation.

GRAPHICAL ABSTRACT

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