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 View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2005-11

AUTHORS

Yu. M. Atroshchenko, I. E. Shakhkel'dyan, O. Ya. Borbulevich, A. N. Shchukin, M. Yu. Antipin, V. N. Khrustalev

ABSTRACT

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. More... »

PAGES

1683-1689

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11178-006-0019-7

DOI

http://dx.doi.org/10.1007/s11178-006-0019-7

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1046182608


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