75541-42-3Relevant 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
Venkatraj,Ponnuswamy,Jeyaraman
scheme or table, p. 110 - 119 (2009/12/04)
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
Stereochemistry of Tetraaryl-3,7-diazabicyclononanes and Tetraaryl-1,3-diazaadamantanes
Quast, Helmut,Mueller, Bodo
, p. 2959 - 2975 (2007/10/02)
By means of paraformaldehyde, the 2,4,6,8-tetraaryl-3,7-diazabicyclononanones 7 = 19 of known constitution have been converted to the 1,3-diazaadamantanes 9 = 17 and 10 = 18, respectively, either directly or after previous Wolff-Kishner reduction.The IR and NMR spectra prove the rel-(2S, 4R, 6R, 8S)-configuration of the diazabicyclononanes 19 and 20 and the rel-(4R, 8S, 9R, 10S)-configuration of the corresponding 1,3-diazaadamantanes 17 and 18.These served as models in an 1H NMR spetroscopic investigation of the diazabicyclononanes 19 and 20, which exist in the chair-chair conformation, one chair having a pair of axial the other a pair of equatorial aryl groups.The reaction of the cis-2,6-diphenylpiperidone 6a with benzaldehyde or 4-methylbenzaldehyde and the reaction of 6b with benzaldehyde inevitably yielded mixtures of type 19, R4 = Ar14-nAr2n(n = 0-4), since in part the aldehydes are incorporated into the piperidones 6.The (equatorial) aryl groups of the piperidones 6 prefer the axial positions in the diazabicyclononanes 19.The diastereoselective formation of the diazabicyclononanes 21 and 22 is compared to that of 8-oxosparteine (27) and traced back to the greater stability of the all-trans-substituted piperidone intermediate trans-28.
