Reaction products from αβ-unsaturated ketones and aliphatic diamines or dithiols

1971 ◽  
Vol 0 (0) ◽  
pp. 3441-3445 ◽  
Author(s):  
Kálmán Hideg ◽  
Douglas Lloyd
1996 ◽  
Vol 61 (12) ◽  
pp. 1805-1814 ◽  
Author(s):  
Ľubomír Šebo ◽  
Juraj Alföldi ◽  
Grety Rihs ◽  
Štefan Toma

The Michael addition of (-)-dimenthyl malonate to eight α,β-unsaturated ketones has been studied. The ratio of diastereomers was calculated on the basis of the 1H NMR spectra of the crude reaction products. The diastereomer excess varied from 10 to 50%, depending on the structure of the starting enone. The pure diastereomer produced by addition of (-)-dimenthyl malonate to 2-benzylidene-1,4-indandione was isolated by repeated crystallization. X-ray analysis has shown that the isomer is (-)-dimenthyl (R)-2-[1-(1,3-dioxoindan-2-yl)-1-phenylmethyl]malonate (5a). The predominating diastereomers of (-)-dimenthyl(3-ferrocenyl-3-oxophenylpropyl)malonate (1a) and (-)-dimenthyl-2-(1-(1,3-dioxo[3]ferrocenophan-2-yl)-1-phenyl malonate (6a) were also isolated in pure state by careful crystallization.


1981 ◽  
Vol 17 (12) ◽  
pp. 1158-1161 ◽  
Author(s):  
Sh. T. Akhmedov ◽  
N. S. Sadykhov ◽  
R. Sh. Akhmedova ◽  
N. S. Zefirov

2005 ◽  
Vol 78 (7) ◽  
pp. 1122-1125 ◽  
Author(s):  
E. V. Fomina ◽  
G. N. Chervyakova ◽  
Yu. A. Kurskii ◽  
A. P. Sineokov

1982 ◽  
Vol 60 (12) ◽  
pp. 1432-1438 ◽  
Author(s):  
H. Olga Hankovszky ◽  
Kálmán Hideg ◽  
László Lex ◽  
Gyula Kulcsár ◽  
H. Anna Halász

The reactions of 1-oxyl-2,2,5,5-tetramethyl-3-pyrroline-3-carboxaldehyde (1), 1-oxyl-2,2,5,5-tetramethyl-3-cyano-3-pyrroline (2), ethyl 1-oxy(-2,2,5,5-tetramethyl-3-pyrroline-3-carbonyl carbonate (3), and N-(1-oxyl-2,2,5,5-tetramethyl-3-pyrroline-3-carbonyl)imidazolide (4) are investigated with several nucleophiles (dialkylcadmium, diethyl sodio-malonate, magnesium enolate of ethyl hydrogen malonate, nitromethane-anion) to obtain α,β-unsaturated ketones, β-ketoesters, or conjugated reaction products. Aldehyde 1 is reacted with several methyl ketones (acetylmethylene-triphenylphosphorane, acetophenone, 2-acetylpyridine, 4-phenyl-3-butyn-2-one) to give spin labeled polyenones. The reaction of 4-(1-oxyl-2,2,5,5-tetramethyl-3-pyrroline-3-yl)-2-buten-2-one (24a) with ethylenediamine gives 7,14-bis-(1-oxyl-2,2,5,5-tetramethyl-3-pyrroline-3-yl)-5,12-dimethyl-1,4,8,11-tetraazatetradeca-7,14-diene biradical (25).


1993 ◽  
Vol 42 (7) ◽  
pp. 1228-1235 ◽  
Author(s):  
L. V. Rybin ◽  
S. V. Osintseva ◽  
A. S. Batsanov ◽  
Yu. T. Struchkov ◽  
P. V. Petrovskii ◽  
...  

1987 ◽  
Vol 52 (4) ◽  
pp. 1021-1025 ◽  
Author(s):  
Mohammad M. Al-Arab ◽  
Ali M. Issa

1,3-Diaryl-2-propene-1-ones I react with arylacetonitriles II in the presence of sodium ethoxide at room temperature to give a single diastereomer of the corresponding 2,3-diaryl-4-aroylbutyronitriles III. The structures of the reaction products were established by infrared, nuclear magnetic resonance, and mass spectral data as well as elemental analysis. The diastereomeric purity was determined by NMR measurements using lanthanide shift reagents. The observed resonances did not show any resolved diastereomeric proton signals.


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