Citation:
ALIREZA Dadrass, ALI Ramazani, AHMAD Poursattar Marjani, HOJJATOLLAH Rahchamani, HASSAN Nasri Koureh, ALI Souldozi, SEPIDEH Samiee, KATARZYNA Ślepokura, TADEUSZ Lis. Synthesis and Structural Characterization of Organophosphorus Ylide-1-(3-nitrophenyl)-2-(triphenyl phosphoranylidene)ethanone[J]. Chinese Journal of Structural Chemistry,
2015, 34(3): 373-378.
doi:
10.14102/j.cnki.0254-5861.2011-0504
Synthesis and Structural Characterization of Organophosphorus Ylide-1-(3-nitrophenyl)-2-(triphenyl phosphoranylidene)ethanone
摘要:
The title compound Ph3P=C(H)C(O)PhNO2 (L) has been prepared by the addition of triphenylphosphine in acetone as solvent to 2-bromo-1-(3-nitrophenyl)ethanone followed by the addition of alkaline solution of sodium hydroxide. The yellow crystals of the title ylide were grown in methanol/chloroform solution by drop method without stirring at room temperature. The solid state structure of ylide has been established by X-ray crystallography analysis. In the molecule of the title compound, the geometry around the P atom is nearly tetrahedral and the O atom is in synperiplanar orientation to the P atom. The nitrophenyl ring is twisted with respect to the plane of the carbonyl group through an angle of 36.6(1)°. The crystal (C26H20NO3P, Mr=425.40) belongs to the monoclinic system, space group P21/n with a=10.889(3), b=14.467(3), c=13.872(4)Å, β=103.08(3)°, V=2128.6(10)Å3, Z=4, T=100(2) K, R=0.059 and wR=0.163 for 3984 observed reflections with I>2σ(I).
English
Synthesis and Structural Characterization of Organophosphorus Ylide-1-(3-nitrophenyl)-2-(triphenyl phosphoranylidene)ethanone
Abstract:
The title compound Ph3P=C(H)C(O)PhNO2 (L) has been prepared by the addition of triphenylphosphine in acetone as solvent to 2-bromo-1-(3-nitrophenyl)ethanone followed by the addition of alkaline solution of sodium hydroxide. The yellow crystals of the title ylide were grown in methanol/chloroform solution by drop method without stirring at room temperature. The solid state structure of ylide has been established by X-ray crystallography analysis. In the molecule of the title compound, the geometry around the P atom is nearly tetrahedral and the O atom is in synperiplanar orientation to the P atom. The nitrophenyl ring is twisted with respect to the plane of the carbonyl group through an angle of 36.6(1)°. The crystal (C26H20NO3P, Mr=425.40) belongs to the monoclinic system, space group P21/n with a=10.889(3), b=14.467(3), c=13.872(4)Å, β=103.08(3)°, V=2128.6(10)Å3, Z=4, T=100(2) K, R=0.059 and wR=0.163 for 3984 observed reflections with I>2σ(I).
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