Heterocyclic Ions From N-Oxides of N-(4-Nitrobenzylidene)-2-cyclopropylaniline and N-(4-Nitrobenzylidene)-2-cyclopropylmethylniline: Formation, Isomerization, and Conversions.

Autor:	Trofimova, E. V., Fedotov, A. N., Gazzaeva, R. A., Mochalov, S. S., Shabarov, Yu. S., Zefirov, N. S.
Předmět:	IONS HYDROBROMIC acid HYDROGEN bromide INORGANIC acids REARRANGEMENTS (Chemistry) HETEROCYCLIC compounds HETEROCYCLIC chemistry
Zdroj:	Chemistry of Heterocyclic Compounds; Jan2003, Vol. 39 Issue 2, p205-212, 8p
Abstrakt:	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-cyclopropylmethylan iline forms the corresponding 2,1 -benzoxazinium and 2,1 -benzoxazepinium salts in a ratio of 1 : 2. The 2,1 -benzoxazepiniumions 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. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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