4-tert-Butyl-2,2-dimethylcyclohexylidene. A surprising lack of stereoselectivity in a 1,2-hydrogen shift to an alkylcarbene

1977 ◽  
Vol 99 (25) ◽  
pp. 8329-8330 ◽  
Author(s):  
Evan P. Kyba ◽  
A. Meredith John
Keyword(s):  
Hydrogen Shift ◽  
Tert Butyl

scholarly journals Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water

2013 ◽  
Vol 9 ◽  
pp. 1713-1717 ◽  
Author(s):  
Daisuke Hirose ◽  
Tsuyoshi Taniguchi
Keyword(s):  
Molecular Oxygen ◽  
Hydrogen Shift ◽  
Tert Butyl

Water induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp3 C–H functionalization by an 1,5-hydrogen shift using tert-butyl nitrite and molecular oxygen. The reaction without water, reported previously, gives nitrated γ-lactols, whereas the reaction in the presence of water produces 4-hydroxy-5-nitropentyl nitrate or 4-hydroxy-3-nitropentyl nitrate derivatives.

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