Microwave-Induced Synthesis of Nitrostilbenes Under Neat Condition

Saravanan, Sivaperuman; Srinivasan, P. C.

doi:10.1081/scc-100103315

Cited by 12 publications

(6 citation statements)

References 8 publications

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“…The products of the reactions were obtained in yields of 19–51%. Low yields obtained in reactions to afford stilbenes through condensation reactions have been reported in the literature. , In addition, the highest yields were obtained for the products containing 2,4-dinitrophenyl groups, due to the fact that 2,4-dinitrotoluene is appreciably more acidic than 4-nitrotoluene. Compound 9a could not be obtained through this methodology.…”

Section: Resultsmentioning

confidence: 88%

Synthesis and Solvatochromism of Substituted 4-(Nitrostyryl)phenolate Dyes

et al. 2015

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4-(Nitrostyryl)phenols 2a-9a were synthesized, and by deprotonation in solution, the solvatochromic phenolates 2b-9b were formed. Their absorption bands in the vis region of the spectra are due to π-π* electronic transitions, of an intramolecular charge-transfer nature, from the electron-donor phenolate toward the electron-acceptor nitroarene moiety. The frontier molecular orbitals and natural bond orbitals were analyzed for the protonated and deprotonated forms. The calculated geometries are in agreement with X-ray structures observed for 4a, 6a, and 8a. The HOMO-LUMO energy gaps suggest that, after their deprotonation, an increase in the electron delocalization is observed. In the protonated compounds, the HOMO is primarily localized over the phenol ring and the C═C bridge. After deprotonation, it extends toward the entire molecule, including the NO2 groups. The solvatochromism of each dye was studied in 28 organic solvents, and it was found that all compounds exhibit a reversal in solvatochromism, which is interpreted in terms of the ability of the media to stabilize their electronic ground and excited states to different extents. The Catalán multiparameter equation is used in the interpretation of the solvatochromic data, revealing that the most important contribution to the solute/solvent interaction is the hydrogen-bond donor acidity of the solvent.

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Section: Resultsmentioning

confidence: 88%

Synthesis and Solvatochromism of Substituted 4-(Nitrostyryl)phenolate Dyes

et al. 2015

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“…A mixture of 2,4-dinitrotoluene [7] (5 mM, 0.9 g) and 4-methyl-3-nitrobenzaldehyde [9,10] (5 mM, 0.8 g) and pyrrolidine (0.106 g, 1. Representative Procedure for the Synthesis of (E ) 4 0 -Methyl-a,2,3 0 ,4,5 0 -pentanitrostilbene (2c)…”

Section: Methodsmentioning

confidence: 99%

“…We report here the first synthesis of (E ) a,2,4-trinitrostilbenes 2a-d by direct nitration of easily available [7] (E ) 2,4-dinitrostilbenes la-e in 55-60% yield, using fuming nitric acid [8] (Sch. 1).…”

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confidence: 99%

Synthesis of (E) α,2,4-Trinitrostilbenes from (E) 2,4-Dinitrostilbenes

Saravanan

Srinivasan

2003

Synthetic Communications

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“…The recommended catalyst is piperidine in a refluxing benzene solution 10 although recently a microwave method using pyrrolidine as the catalyst, has been reported. 11 In our work we replaced the benzene with pyridine and retained the piperidine as a catalyst. These conditions which were successful with 2,4-dinitrotoluene and a series of aldehydes, gave trans-stilbenes (see Table 1).…”

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confidence: 99%