Spontaneous generation of chirality and chiroptical spectra of N-nitroso-2,4-diaryl-3-azabicyclo[3.3.1]nonanes
The crystal structures of several bicyclic N-nitrosamines indicate that they crystallize in the chiral (Sohncke) space group P212 121 as conglomerates. This allows the resolution of these compounds by manual picking of the
Olszewska, Teresa,Milewska, Maria J.,Gdaniec, Maria,Polonski, Tadeusz
body text
p. 278 - 283
(2012/06/15)
Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agents
Libraries of 1-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/O-methyloximes 1-14/15-28/29-42 and 7-methyl-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones/oximes/O-methyloximes 43-48/49-54/55-60 were synthesized and their stereochemistry was establis
Parthiban, Paramasivam,Rathika, Paramasivam,Ramkumar, Venkatachalam,Son, Se Mo,Jeong, Yeon Tae
supporting information; experimental part
p. 1642 - 1647
(2010/06/19)
Structure, conformation, and stereodynamics of N-nitroso-2,4-diaryl-3-azabicyclo[3.3.1]nonanes and N-nitroso-2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones
The variable temperature 1H, 13C, and 19F NMR spectra were measured for the title N-nitrosamines. The observed unusually low N-N rotation barriers (12-15 kcal/mol) result from a significant deviation of the nitrosamino system from planarity. A pyramidal character of the amino nitrogen was confirmed by the X-ray crystal structures of two compounds and by bathochromic shifts of the n-π* absorption bands in the UV spectra. The nonplanarity of the nitrosamino moiety is due to the strong pseudoallylic A(1,3) strain caused by the steric interaction of the NNO group with the neighboring aryl substituents fixed in the equatorial positions of the bicyclic skeleton. In addition, the barriers to the C-C rotation of aryl groups were examined at temperatures lower than required to "freeze" the N-N rotation and different ΔG? values were observed for the aryls oriented syn and anti to the nitroso oxygen.
Po?on?ski, Tadeusz,Pham, Marzena,Milewska, Maria J.,Gdaniec, Maria
p. 3766 - 3772
(2007/10/03)
Synthesis of 3,4,5,6,7,8-Hexahydro-2H-4a,8-alkanopyridopyrimidines from N,N'-Dibenzylidenephenylmethanediamines and Some 2-Substituted Cyclanones
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Takajo, Tokiharu,Kambe, Satoshi,Ando, Wataru
p. 655 - 657
(2007/10/02)
Synthesis of Some 3-Azabicyclononane Derivatives
4-tert-Butylcyclohexanone (VII) on condensation with benzaldehyde and ammonium acetate yields 7-tert-butyl-2,4-diphenyl-3-azabicyclononan-9-one (VIII).Similary, 2-methylcyclohexanone, 4-methylcyclohexanone and 2-decalone afford 1-methyl-2,4-dipheny
Jeyaraman, R.,Chockalingam, Kn.,Rajendran, T.
p. 519 - 521
(2007/10/02)
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