Structural study of 3-azabicyclo[3.3.1]nonane derivatives functionalized at 1 and/or 9-positions by molecular mechanics calculations and NMR spectroscopy

✍ Scribed by Ma Selma Arias-Pérez; A. Alejo; A. Maroto

• Book ID: 104208032
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 650 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00832-6

✦ Synopsis

nonan-9-ones, 1-3, l-alkoxycarbonyl derivates, 4, 5 and aand fl3methyl-3-azabicyclo[3.3.1]nonan-9-ols, 6, 7, have been studied by means of the molecular mechanics (MMX) method and ~H, t3C-NMR spectroscopy. Experimental data fit well with theoreticalcalculations. It is found that the conformational behaviour of the bicyclic system is governed mainly by sterie factors and a flattened chair-chair conformation bearing the N-substituent in the equatorial position (CC-fl) is always preferred. A monoconformatioual character can be reasonably assumed except for 3-methyl-3azabicyclo[3.3.1lnonan-9fl-ol, 7, in non polar solvents where the BC-a form should amount to about 150 of the equilibrium mixture.