Synthesis and structure of nitro derivatives of 4-(2-thienyl)-3-buten-2-one

Panfilova, L. V.; Antipin, M. Yu.; Churkin, Yu. D.; Struchkov, Yu. T.

doi:10.1007/bf00473839

Cited by 2 publications

(2 citation statements)

References 3 publications

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“…Similarly, the X-rays of 2a and 2d (yellow crystals from EtOAc) , showed a trans-arrangement of the nitro group with the furyl- and the thienyl-ring, respectively (Table , entries 1 and 2) . They also showed the entire π system to be almost planar with CCNO dihedral absolute values of about 4° and 10° for 2a and 2d , respectively.…”

Section: Resultsmentioning

confidence: 86%

Synthesis, Structure, and E−Z Isomerization of β-(Hetero)aryl-α-nitro-α,β-enals

et al. 2008

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The first general methodology for the gram-scale preparation of previously overlooked beta-(hetero)aryl-alpha-nitro-alpha,beta-enals (3) is reported. Condensation of (hetero)aromatic aldehydes with 2-nitroethanol gave the E-isomers of uncommon beta-(hetero)aryl-alpha-hydroxymethyl-alpha,beta-unsatured-nitroalkenes (2), as determined by NOE and X-ray studies. alpha-Nitro-alpha,beta-enals 3 were subsequently obtained by hypervalent iodine oxidation of 2 as E-Z-mixtures in solid form. They showed varied stability and solvent-dependent thermal-promoted and photopromoted E-Z interconversion. Starting with furfural, experimental conditions were developed to prepare the corresponding nitroenal 3a enriched in either the E or the Z isomer: E-3a/Z-3a approximately 90/10 and 20/80, respectively. In contrast with other structurally related compounds, nitroenals 3 have their (hetero)aryl-vinyl unit and their formyl and nitro groups all in a planar arrangement, both in solid form and in solution; accordingly, they are colored compounds with predicted high dipole moments. As deduced from solution-NMR and X-ray data, the C=C and the C=O double bonds in 3 are exclusively s- cis-oriented; this disposition corresponds in fact to the DFT-computed most stable conformer.

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Section: Resultsmentioning

confidence: 86%

Synthesis, Structure, and E−Z Isomerization of β-(Hetero)aryl-α-nitro-α,β-enals

et al. 2008

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“…Benzene was purified using standard procedure. In the calculations of dipole moments according to vector-additive scheme we used the following bond angle values: CCBr = 121° [14], CC=O = 120°, CC-O = 120°, CCN = 121° [15], CCH 1 = 118° [15], CCH 2 = 117° [15], as well as the bonds and groups moments: m(C sp2 -Br) = 0.66 D calculated from l exp CH 2 =CHBr [16]; m(C sp2 -NO 2 ) = 2.81 D calculated from l exp CH 2 =CHNO 2 [16]; m(H-C sp2 ) = 0.70 D [12]; m(C sp3 -C sp2 ) = 0.78 D calculated from l exp C 3 H 6 [16]; m(C = O) = 1.94 D [17]; m(C-O) = 0.18 D calculated from l exp CH 3 C(O)OEt, m(Et-O) = 1.11 D [16]; m(C-Cl 3 ) = 1.26 D calculated from l exp 1,1,1-trichloroethane [18]. Quantum chemical calculations were carried out by the GAUSSIAN 03 program [19] at the B3LYP level of the hybrid density functional theory.…”

Section: Methodsmentioning

confidence: 99%

Conformational analysis of 2-substituted nitroethenes

et al. 2010

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Experimental and theoretical conformational analysis of polyfunctional 2-substituted nitroethenes was carried out by the method of dipole moments and density functional theory calculations. It was established that the nitro and ester (or trichloromethyl) groups are transarranged in the molecules of 2-trichloromethyl-(ethoxycarbonyl)-1-nitro-and 1-bromo-1-nitroethenes, i.e., nitroalkenes have E-configuration, their bromo-containing analogues have Z-configuration, and s-cis-orientation of the C=C and C=O double bonds is preferred for nitroacrylates. 2,3-Dibromo-3-nitroacrylates have untrivial Z-configuration in solution.

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Synthesis and structure of nitro derivatives of 4-(2-thienyl)-3-buten-2-one

Cited by 2 publications

References 3 publications

Synthesis, Structure, and E−Z Isomerization of β-(Hetero)aryl-α-nitro-α,β-enals

Synthesis, Structure, and E−Z Isomerization of β-(Hetero)aryl-α-nitro-α,β-enals

Conformational analysis of 2-substituted nitroethenes

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