Synthesis of Nitriles from Primary Amides or Aldoximes under Conditions of a Catalytic Swern Oxidation

2018 ◽  
Vol 83 (20) ◽  
pp. 12939-12944 ◽  
Author(s):  
Rui Ding ◽  
Yongguo Liu ◽  
Mengru Han ◽  
Wenyi Jiao ◽  
Jiaqi Li ◽  
...  
Keyword(s):  
Swern Oxidation

Swern oxidation

2003 ◽  
pp. 402-403
Author(s):  
Jie Jack Li
Keyword(s):  
Swern Oxidation

Swern Oxidation

2021 ◽  
pp. 533-535
Author(s):  
Jie Jack Li
Keyword(s):  
Swern Oxidation

Cyclopropenium-Activated DMSO for Swern-Type Oxidation

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 329-332 ◽  
Author(s):  
Tianfo Guo ◽  
Yu Gao ◽  
Zhenjiang Li ◽  
Jingjing Liu ◽  
Kai Guo
Keyword(s):  
Conventional Method ◽  
Carbonyl Compounds ◽  
Oxalyl Chloride ◽  
Fast Reactions ◽  
Broad Scope ◽  
New Type ◽  
High Yields ◽  
Swern Oxidation ◽  
Easy Operation

Swern oxidation is widely used to convert alcohols into their corresponding carbonyl compounds. However, the conventional method with use of the volatile oxalyl chloride as an activator requires the reaction to be conducted below −60 °C. We discovered that 3,3-dichloro-1,2-diphenylcyclopropene (DDC) can be used as a new activator for Swern-type oxidations of alcohols, which can be conducted at −20 °C. This new protocol features mild and fast reactions with easy operation. Furthermore, the activator DDC is easy to handle, and diphenylcyclopropenone can be recovered quantitively. This new type of Swern oxidation shows a broad scope of substrates including benzylic, allylic, aliphatic, and biobased alcohols, and gives high yields of up to 93%.

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