Reductive debromination and coupling reaction in the thermolysis of 5-bromouracils in N,N-dialkylamides. Cleavage of the C(5)–bromine bond by an initial electron-transfer process

1981 ◽  
pp. 3114-3117 ◽  
Author(s):  
Magiochi Sako ◽  
Mikio Suzuki ◽  
Miyuki Tanabe ◽  
Yoshifumi Maki
Keyword(s):  
Electron Transfer ◽  
Transfer Process ◽  
Coupling Reaction ◽  
Electron Transfer Process ◽  
Initial Electron

Oxidative Functionalization of Cyclic N-Arylamines with Nitromethane and TMSCN Using the T-HYDRO/t-BuOK System

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 617-624 ◽  
Author(s):  
Mariappan Periasamy ◽  
Gunda Rao
Keyword(s):  
Electron Transfer ◽  
Transfer Process ◽  
Electron Transfer Process ◽  
Oxidative Functionalization ◽  
Butyl Hydroperoxide ◽  
Tert Butyl ◽  
Initial Electron ◽  
Tert Butyl Hydroperoxide ◽  
Iminium Ion

Tertiary cyclic N-arylamines react with nitromethane in the presence of the tert-butyl hydroperoxide (T-HYDRO)/t-BuOK system to give β-nitroamines in up to 90% yield. When TMSCN is used in place of nitromethane, α-aminonitriles are obtained in up to 96% yield. The method is suitable for several unactivated cyclic arylamine substrates. These transformations are rationalized considering the formation of the corresponding iminium ion intermediates via an initial electron transfer process.

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