640282-43-5Relevant academic research and scientific papers
Heterocyclic ions from N-oxides of N-(4-nitrobenzylidene)-2-cyclopropylaniline and N-(4-nitrobenzylidene)-2-cyclopropylmethylaniline: Formation, isomerization, and conversions
Trofimova,Fedotov,Gazzaeva,Mochalov,Shabarov,Zefirov
, p. 205 - 212 (2003)
The N-oxide of N-(4-nitrobenzylidene)-2-cyclopropylaniline is converted by the action of strong acids into the corresponding 2,1-benzoxazinium derivative. Under identical conditions the N-oxide of N-(4-nitrobenzylidene)-2-cyclopropylmethylaniline forms the corresponding 2,1-benzoxazinium and 2,1-benzoxazepinium salts in a ratio of 1: 2. The 2,1-benzoxazepinium ions are thermodynamically less stable and are isomerized with time into 2,1-benzoxazinium ions. Treatment of 2,1-benzoxazinium salts with hydrobromic acid solution and subsequent neutralization leads to o-(2-hydroxyalkyl)anilines and p-nitrobenzaldehyde. The effect of the nature of the ortho substituent on the direction of the conversions of the corresponding arylcyclopropanes is discussed.
