Intramolecular ring closure of α,β-epoxy sulfoxides with hydroxyl group: A novel synthesis of 2-acyl cyclic ethers and 3-keto cyclic ethers

1987 ◽  
Vol 28 (23) ◽  
pp. 2603-2606 ◽  
Author(s):  
Tsuyoshi Satoh ◽  
Ken-ichi Iwamoto ◽  
Koji Yamakawa
Keyword(s):  
Ring Closure ◽  
Hydroxyl Group ◽  
Cyclic Ethers ◽  
Novel Synthesis ◽  
Group A ◽  
Intramolecular Ring

scholarly journals TfOH-Promoted Reaction of 2,4-Diaryl-1,1,1-Trifluorobut-3-yn-2-oles with Arenes: Synthesis of 1,3-Diaryl-1-CF3-Indenes and Versatility of the Reaction Mechanisms

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3079 ◽  
Author(s):  
Aleksey V. Zerov ◽  
Anna N. Kazakova ◽  
Irina A. Boyarskaya ◽  
Taras L. Panikorovskii ◽  
Vitalii V. Suslonov ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Reaction Mechanisms ◽  
Room Temperature ◽  
Ring Closure ◽  
Nucleophilic Attack ◽  
New Process ◽  
Intramolecular Ring ◽  
Propargyl Alcohols

The TfOH-mediated reactions of 2,4-diaryl-1,1,1-trifluorobut-3-yn-2-oles (CF3-substituted diaryl propargyl alcohols) with arenes in CH2Cl2 afford 1,3-diaryl-1-CF3-indenes in yields up to 84%. This new process for synthesis of such CF3-indenes is complete at room temperature within one hour. The synthetic potential, scope, and limitations of this reaction were illustrated by more than 70 examples. The proposed reaction mechanism invokes the formation of highly reactive CF3-propargyl cation intermediates that can be trapped at the two mesomeric positions by the intermolecular nucleophilic attack of an arene partner with a subsequent intramolecular ring closure.

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