The SYNTHESIS OF Α,α-Disubstituted SUCCINIC ACIDS FROM ETHYL ALKYLIDENECYANOACETATES

Cragoe, E. J.; Robb, Charles M.; Sprague, James M.

doi:10.1021/jo01148a024

Cited by 52 publications

(21 citation statements)

References 9 publications

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“…According to the fact that Knoevenagel condensation is classically catalysed under basic conditions, a proposed plausible mechanism is presented for the reaction of various aldehydes with malononitrile in Scheme . In this context, the C═N groups of the Schiff base ligand can act as highly reactive base sites.…”

Section: Resultsmentioning

confidence: 99%

Efficient and recyclable novel Ni‐based metal–organic framework nanostructure as catalyst for the cascade reaction of alcohol oxidation–Knoevenagel condensation

Aryanejad

Bagherzade

Farrokhi

2017

Applied Organom Chemis

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A novel Ni‐based metal–organic framework (Ni‐MOF) with a Schiff base ligand as an organic linker, Ni3(bdda)2(OAc)2⋅6H2O (H2bdda = 4,4′‐[benzene‐1,4‐diylbis(methylylidenenitrilo)]dibenzoic acid), was synthesized and characterized using powder X‐ray powder diffraction, thermogravimetric analysis, Brunauer–Emmett–Teller measurements, inductively coupled plasma atomic emission spectroscopy, transmission electron microscopy, elemental analysis and Fourier transform infrared spectroscopy. The synthesized Ni‐MOF exhibited a high catalytic activity in benzyl alcohol oxidation using tert‐butyl hydroperoxide under solvent‐free conditions. Also, the efficiency of the catalyst was investigated in the cascade reaction of oxidation–Knoevanagel condensation under mild conditions. The Ni‐MOF catalyst could be recovered and reused four times without significant reduction in its catalytic activity.

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Section: Resultsmentioning

confidence: 99%

Efficient and recyclable novel Ni‐based metal–organic framework nanostructure as catalyst for the cascade reaction of alcohol oxidation–Knoevenagel condensation

Aryanejad

Bagherzade

Farrokhi

2017

Applied Organom Chemis

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“…The condensation of benzophenone 1a with ethyl cyanoacetate under Knoevenagel conditions gave ethyl (α-cyano-β,β-diphenyl)acrylate 2a 11 following the literature procedure, with a slight modification. We found that the use of a three-fold excess of ammonium acetate as a catalyst leads to the cyanoacrylate 2a with a yield of 90% compared to the previously reported 41% yield.…”

Section: Resultsmentioning

confidence: 99%

“…11 Diphenylsuccinic acid 4a was cyclized to the anhydride 5a by treatment with acetyl chloride. Subsequent reaction of 5a with benzyl amine gave the succinimic acid 6a, which was cyclized to succinimide 7a in refluxing acetic anhydride (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 3,3-diarylpyrrolidines from diaryl ketones

Katritzky¹,

Nair²,

Witek³

et al. 2003

Arkivoc

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“…This mixture was vigorously refluxed and ammonium acetate (12g, 0.16 mol) was added in 1.5 g portions at 3-4 hour intervals. 16 The progress of the reaction was monitored by thin layer chromatography, using a silica gel sheet as the adsorbent and a mixture of carbon tetrachloride--chloroform A 500 ml 3-neck round-bottom flask was charged with ethyl 4-ethyl-rx-cyano-fJ-phenylcinnamate ( 40 g, 0.13 mol), carbon tetrachloride (170m!) and NBS (25.7 g, 0.14mol).…”

Section: -mentioning

confidence: 99%

“…The reaction mixture was vigorously refluxed and ammonium acetate (0.41 g, 5.3 mmol) was added in 0.1 g portions at 4-17 hour intervals. 16 The progress of reaction was checked by thin-layer chromatography (TLC), using a silica gel sheet as an adsorbent and a mixture of carbon tetrachloride-chloroform (2: 1 volume ratio) as a solvent.…”

Section: -mentioning

confidence: 99%

Functional Polymers. VII. Ethyl 4-Vinyl-α-cyano-β-phenylcinnamate

Sumida

Vogl

1981

Polym J

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ABSTRACT:Ethyl 4-vinyl-ct-cyano-/1-phenylcinnamate was prepared by a five step synthesis from 4-ethylbenzoic acid in an overall yield of 20%. The acid chloride of 4-ethylbenzoic acid was condensed with benzene to 4-ethylbenzophenone. The most critical step in the synthesis was the Knoevenagel condensation of 4-ethylbenzophenone with ethyl cyanoacetate which was accomplished with ammonium acetate as the catalyst. Ethyl 4-ethyl-ct-cyano-/1-phenylcinnamate was readily brominated with N-bromosuccinimide and the bromination product, ethyl 4-(1-bromoethyl)-ct-cyano-p-phenylcinnamate was dehydrobrominated. Ethyl 4-vinyl-ct-cyano-Pphenylcinnamate consists of a mixture of cis and trans isomers of nearly equal amounts as indicated in 1 H nuclear magnetic resonance and 13 C nuclear magnetic resonance spectroscopy. This new monomer was homopolymerized and copolymerized with styrene and methyl methacrylate with radical initiators.KEY WORDSPhoto-chemical reactions which occur in polymers on exposure to solar radiation cause damage to the physical and mechanical properties and to the appearance of polymers. When used outdoors, polymers are usually protected by adding ultraviolet (UV) stabilizers which can absorb most of the damaging radiation and reemit it in a form not harmful to the polymer. Low-molecular-weight UV absorbing compounds are used for the photo stabilization of polymers1. 2 with the most effective compounds being salicylates, 2,4-dihydroxybenzophenones, 2-hydroxyphenylbenzotriazoles or other more exotic, noncolor forming compounds. 3 • 4 More recently, interest in polymeric UV stabilizers has been directed towards the synthesis of vinyl substituted monomers which have groups capable of UV absorption. 3 .4 The successful synthesis of 3-vinyl, 5 4-vinyl, 6 and 5-vinylsalicylic acid derivatives 7 has been reported.The synthesis of 2,4-dihydroxy-4' -vinylbenzo- Polym. Sci., Polym. Chern. Ed., 18, 2755(1980. phenone, a powerful UV absorber, was accomplished in about a 14% overall yield from 4-ethylbenzoic acid. 8 · 9 The last three steps consisted of bromination of 2,4-diacetoxy-4' -ethylbenzophenone with N-bromosuccinimide followed by dehydrobromination and hydrolysis to 2,4-dihydroxy-4' -vinylbenzophenone. Esters of a-cyano-{3-phenylcinnamic acid have also been used in the past as UV stabilizers, 10 • 11 especially when UV absorbers with free phenolic groups were undesirable. Certain polymers, especially polyacetals, are sensitive to high concentrations of phenol containing UV stabilizers. At temperatures above 200°C where polyacetals are fabricated, ethyl a-cyano-{3-phenylcinnamate or the methyl ester have been found to have significant volatility and significant losses in stabilizer capacity. Consequently, attempts were made to decrease the volatility of a-cyano-{3-phenylcinnamates without diminishing their effectiveness by increasing their molecular weights 12 by preparing bisesters of glycols and a-cyano-{3-phenylcinnamic acid; the useful-521

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The SYNTHESIS OF Α,α-Disubstituted SUCCINIC ACIDS FROM ETHYL ALKYLIDENECYANOACETATES

Cited by 52 publications

References 9 publications

Efficient and recyclable novel Ni‐based metal–organic framework nanostructure as catalyst for the cascade reaction of alcohol oxidation–Knoevenagel condensation

Efficient and recyclable novel Ni‐based metal–organic framework nanostructure as catalyst for the cascade reaction of alcohol oxidation–Knoevenagel condensation

Synthesis of 3,3-diarylpyrrolidines from diaryl ketones

Functional Polymers. VII. Ethyl 4-Vinyl-α-cyano-β-phenylcinnamate

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