Formation of Isomeric 3-Azabicyclo[3.3.1]nonanes in a Reaction of 1-(2-Hydroxyethoxy)-2,4-dinitrobenzene with Sodium Borohydride, Formaldehyde, and Methylamine.

Autor: Atroshchenko, Yu. M., Shakhkel'dyan, I. E., Borbulevich, O. Ya., Shchukin, A. N., Antipin, M. Yu., Khrustalev, V. N.
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Zdroj: Russian Journal of Organic Chemistry; Nov2005, Vol. 41 Issue 11, p1683-1689, 7p
Abstrakt: Anionic hydride adduct of 1-(2-hydroxyethoxy)-2,4-dinitrobenzene was brought into a double Mannich condensation with formaldehyde and methylamine to furnish a mixture of isomeric 3-azabicyclo[3.3.1]nonanes: 3-methyl-6-(2-hydroxyethoxy)-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene and 3-methyl-6,6-ethylenedioxy-1,7-dinitro-3-azabicyclo[3.3.1]nonane. By means of NMR spectroscopy, X-ray difraction analysis, and quantum chemistry (PM3) we demonstrated that the spirocyclic isomer had chair-chair conformation with diequatorial orientation of substituents in positions 3 and 7. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index