tert‐Butyl Hydroperoxide‐Initiated Radical Cyclization of 1‐(allyloxy)‐2‐(1‐arylvinyl)benzenes with Sulfinic Acids to Access Sulfonated Benzoxepines

2021 ◽  
Author(s):  
Nengneng Zhou ◽  
Kaimo Kuang ◽  
Meixia Wu ◽  
Sixin Wu ◽  
Qiankun Xu ◽  
...  
Keyword(s):  
Radical Cyclization ◽  
Butyl Hydroperoxide ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide ◽  
Sulfinic Acids

Synthesis of 3-Phenylsulfonylcoumarins by Cyclisation of Phenyl Propiolates with Sulfinic Acids or Sodium Sulfinates

2018 ◽  
Vol 42 (10) ◽  
pp. 515-520
Author(s):  
Hexiang Ren ◽  
Yuanyang Mu ◽  
Ming Zhang ◽  
Ai Qin Zhang
Keyword(s):  
Silver Nitrate ◽  
Functional Groups ◽  
Potassium Iodide ◽  
Potassium Persulfate ◽  
Butyl Hydroperoxide ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide ◽  
Migration Mechanism ◽  
Sulfinic Acids

Methods for the synthesis of 3-phenylsulfonylcoumarins by radical sulfonylation cyclisation of phenyl propiolates with sulfinic acids or sodium sulfinates as sulfonyl sources have been developed. A combination of potassium persulfate as oxidant and silver nitrate as catalyst, or tert-butyl hydroperoxide as oxidant and potassium iodide as catalyst were used. The products were formed by an ipso-cyclisation/1,2-ester migration mechanism. The toleration of functional groups is broad and the yield is up to 96%.

Tetrabutylammonium Iodide Catalyzed Synthesis of Allylic Ester with tert-Butyl Hydroperoxide as an Oxidant

2012 ◽  
Vol 14 (13) ◽  
pp. 3384-3387 ◽  
Author(s):  
Erbo Shi ◽  
Ying Shao ◽  
Shulin Chen ◽  
Huayou Hu ◽  
Zhaojun Liu ◽  
...  
Keyword(s):  
Butyl Hydroperoxide ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide ◽  
Tetrabutylammonium Iodide
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