Structural study of 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9β-ol

The infrared spectra in several media and the crystal structure of 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]-nonan-9β-ol ( I ) (Scheme I) have been determined, in order to complete the structural study described for the title compound from the ¹H and ¹³C nmr data [1]. The bicyclic system adopts a flattened chair-chair conformation in which the cyclohexane ring is more flattened. The methyl and phenyl groups are in equatorial positions and the OH group in an axial position with respect to the piperidine ring.     

Crystal and molecular structure of 2,4-diphenyl23-(3-phenylpropine-2-yl) -3-azabicyclo[3.3. I] nonane-9-ol

S. M. Kirov Kazakh State University, Chemical Institute for Oil and Natural Salts, Academy of Sciences of the Kazakh SSR, M. V. Lomonsov State University, Moscow. Translated from Zhurnal Strukturnoi Khimii, Vol. 31, No. 1, pp. 192–195, January–February, 1990.     

Crystal and molecular structure of 6,6-dimethyl-cis-2,4-diphenyl-3-aza-7-oxabicyclo[3.3.1]nonan-9-one

A method is presented for synthesizing 6,6-dimethyl-2,4-diphenyl-3-aza-7-oxabicyclo[3.3.1]nonan-9-one. The x-ray structure shows that the compound in the crystal exists in the chair-boat conformation with the piperidine ring in the boat form. The two phenyl substituents in the 2- and 4-positions are responsible for such a conformation.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1400–1402, October, 1990.     

X-ray diffraction study of 2,4-diphenyl-9-ethynyl-3-azabicyclo-[3.3.1]nonan-9-ol

Kazakh State University. Translated from Zhurnal Strukturnoi Khimii, Vol. 34, No. 2. pp. 179–181, March–April, 1993.     

Domain structure of organic crystals. Crystal structure of 3-bromobicyclo[3. 3. 1]non-2-en-4-one

M. V. Lomonosov Moscow State University. Translated from Zhurnal Strukturnoi Khimii, Vol. 31, No. 6, pp. 104–107, November–December, 1990.     

Epoxidation of 2-azabicyclo[2.2.1]hept-5-en-3-one

Epoxidation of 2-azabicyclo[2.2.1]hept-5-en-3-one has been performed in high yield with potassium hydrogen persulfate at pH 6, ¹H nmr data indicate an exo stereoconfiguration of the epoxide.     

Spectroscopic study of 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-α(β)-ols

3-Methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-α(β)-ols have been synthesized and studied by ir, ¹H and ¹³C nmr spectroscopy. In deuteriochloroform and perdeuteriobenzene solutions, these compounds adopt a flattened chair-chair conformation in which the cyclohexane ring is more flattened. From the ¹H and ¹³C nmr data, several stereoelectronic effects have been deduced. The complete and unambiguous assignment of all protons of the 3-azabicyclo[3.3.1]nonane system, not described up to date, has been carried out.     

Crystal and molecular structure of 1,5-diphenyl-3,7-diallyl-3,7-diazabicyclo[3.3.1]nonane-9-one

S. M. Kirov Kazakh State University. Chemical Institute for Oil and Natural Salts, Academy of Sciences of the Kazakh SSR. M. V. Lomonosov State University, Moscow. Translated from Zhurnal Strukturnoi Khimii, Vol. 31, No. 1, pp. 189–192, January–February, 1990.     

Synthesis and conformational analysis of 6-substituted-3-azabicyclo[3,3,1]nonanes

6-hydroxy substituted 3-tosyl-3-aza-bicyclo[3,3,1]nonan-9-ones 2a and 2b are obtained directly via acrolein addition to N-Ts-piperidine pyrrolidine enamine. From ¹H NMR spectral data of a series of derivatives a preferred twin-chair conformation for the adducts is indicated. This conclusion is supported both by studies on the elimination of the 6-OR group and on the reduction of the C₉-oxo function. Anomalous formation of sultone 10 is also noted.     

Synthesis of N-substituted 9-[2-(3,4-methylenedioxyphenyl)-2-oxoethyl]-1,5-dinitro-7,8-benzo-3-azabicyclo[3.3.1]non-7-en-6-ones

Aminomethylation has been accomplished of the anionic Yanovskii adduct of 2,4-dinitronaphthol and 3,4-dimethylenedioxyacetophenone. The structure of the 3-substituted 9-[2-(3,4-methylenedioxyphenyl)-2-oxoethyl]-1,5-dinitro-7,8-benzo-3-azabicylo[3.3.1]non-7-en-6-one was determined by two-dimensional homo-and heteronuclear correlation spectroscopy. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, 1382–1389, September 2007.     

Crystal and molecular structure of 1-azabicyclo[3.2.0]heptane-1-methyl chloride

The structure of the compound, 1-azabicyclo[3.2.0]heptane-1-methyl chloride has been determined by a single crystal x-ray diffraction study. The compound crystallizes in space group C_mcm with four formula weights in a unit cell of dimensions a = 8.53, b = 10.30, c = 9.27 ± .01 Å. The molecular cations fit in large holes between the chloride anions and consequently are disordered about the cation positions. The five-membered ring portion is non-planar and bears a strong resemplance to other five-membered rings in bicyclic-fused compounds. The azetidine portion of the molecule is planar. The basic fused ring structure is contrasted to that found in penicillin salts. A final value of R = 0.10₆ for the 305 independent reflections was obtained.     

Conformational effect in 2,4-diphenyl-3-aza-6,6-dimethyl-7-oxabicyclo [3.3.1]nonan-9-ol C21H25O2N

Kazakh State University. Translated from Zhurnal Strukturnoi Khimii, Vol. 32, No. 5, pp. 167–169, September–October, 1991.     

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(1)

The variable temperature (1)H, (13)C, and (19)F 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-pi 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 DeltaG() values were observed for the aryls oriented syn and anti to the nitroso oxygen.     

Crystal and molecular structure of 2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiazepine

A. Mickiewic Poznan University. A. M. Gor'kii Khar'kov State University. Translated from Zhurnal Strukturnoi Khimii, Vol. 30, No. 3, pp. 187–190, May–June, 1989.