78255-62-6

Upstream product

• 34025-58-6 2,4-diphenyl-3-azabicyclo<3.3.1>nonan-9-one 
• 100-52-7 benzaldehyde 
• 108-94-1 cyclohexanone 
• 57794-27-1 rel-(1S,2S,4R,5R)-2,4-Diphenyl-3-azabicyclo<3.3.1>nonan-9-on 

Downstream Products

• 1207518-75-9 N-benzoyl-r-2,c-4-diphenyl-3-azabicyclo[3.3.1]nonane 
• 1207518-74-8 N-chloroacetyl-r-2,c-4-diphenyl-3-azabicyclo[3.3.1]nonane 
• 88365-73-5 rel-(1R,4R,5S)-2,4-Diphenyl-3-azabicyclo<3.3.1>non-2-en 
• 88365-72-4 rel-(1R,4R,5S)-2,4-Diphenyl-3-azabicyclo<3.3.1>non-2-enhydrochlorid 
• 88365-68-8 rel-(1R,2S,4R,5S)-3-Chlor-2,4-diphenyl-3-azabicyclo<3.3.1>nonan 

Relevant academic research and scientific papers

Conformational study of N-acyl-r-2-c-4-diphenyl-3-azabicyclo[3.3.1]nonanes and N3,N7-diformyl-r-2,c-4,t-6,t-8-tetraphenyl-3,7- diazabicyclo[3.3.1]nonane by NMR spectroscopy and semi-empirical molecular orbital calculations

The stereochemistry and stercodynamics of N-chloroacetyl- and N-benzoyl-r-2,c-4- diphenyl-3-azabicyclo[3.3.l]-nonanes (7 and 8) and N 3,N7-diformyl-r-2,c-4,t-6,t-8-tetraphenyl- 3,7-diazabicyclo[3.3.l]nonane 11 have been studied using

N-Chlorination and Dehydrochlorination of Aryl-substituted Piperidines, 3-Azabicyclononanes, and 3,7-Diazabicyclononanes. Synthesis of the First 3,7-Diazanoradamantane.

The N-chloropiperidine derivatives 4b - 6b, 7 and 8 were obtained by N-chlorination using tert-butyl hypochlorite.While dehydrochlorination of 4b and 8 required potassium hydroxide and tert-butoxide, respectively, 5b and 7 eliminated hydrogen chloride at temperatures as low as 20 - 25 deg C even in the absence of base.The N-chloro compound 6b lost hydrogen chloride in boiling chlorobenzene.As expected, the N-chloropiperidine 4b and the N-chloro-3-azabicyclononanes 5b, 6b formed the tetrahydropyridine 9 and the bicyclic iminium chlorides 10 * HCl and 11 * HCl, respectively.The latter were converted into free bases 10 and 11.In contrast, on dehydrochlorination the 3,7-diazabicyclononane ring system of the N,N'- dichloro compound 8 was degraded to the 2,6-bis(4-methylphenyl)pyridine (15).Surprisingly, the spontaneous dehydrochlorination of the 3-chloro-3,7-diazabicyclononane 7 produced the highly strained 3,7-diazanoradamantane 12.Its structure was assigned on the basis of high field proton and carbon-13 NMR spectra, nuclear Overhauser difference spectroscopy, and the temperature dependence of the proton and carbon-13 NMR spectra resulting from slow rotation of the 4-methylphenyl groups.The barrier of rotation for the 1,3-diaxial oriented 4-methylphenyl groups at C-6,8 was found to be ΔG*247 = 50 +/- 1 kJ * mol-1.