Synthese von Thiophen‐ und Pyrrolderivaten

Paal, C.

doi:10.1002/cber.18850180175

Cited by 451 publications

(127 citation statements)

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“…Pyrrole based compounds were prepared through the Paal-Knorr reaction [37,38], by reacting a primary amine with 2,5-HD, as schematically shown in Fig. 1.…”

Section: Resultsmentioning

confidence: 99%

“…Classical methods for the synthesis of pyrroles are Piloty [36] Paal-Knorr [37,38], Barton-Zard [39], and Hantzsch [40], syntheses. Nowadays, new approaches involving the use of transition-metal intermediates [41], multicomponent reactions [42], and reductive couplings [43] are documented.…”

Section: Introductionmentioning

confidence: 99%

“…Nowadays, new approaches involving the use of transition-metal intermediates [41], multicomponent reactions [42], and reductive couplings [43] are documented. The most used procedure is still the Paal-Knorr reaction [37,38]. Paal and Knorr independently used 1,4-dicarbonyl compounds, primary amine and weak mineral acid catalyst.…”

Section: Introductionmentioning

confidence: 99%

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Facile and sustainable functionalization of graphene layers with pyrrole compounds

Barbera

Bernardi

Palazzolo

et al. 2017

Pure and Applied Chemistry

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A facile and sustainable functionalization of graphene layers was performed with pyrrole compounds (PyC) prepared through the Paal-Knorr reaction of a primary amine with 2,5-hexanedione. A good number of primary amines were used: hexanamine, dodecanamine, octadecanamine, 2-aminoacetic acid, 2-amino-1,3-propanediol, 3-(triethoxysilyl)propan-1-amine. The reactions were characterized by good yield, up to 96 %, and indeed satisfactory atom efficiency, up to 80 %. The functionalization of graphene layers was obtained by mixing PyC with a high surface area graphite and heating at a temperature range from 130 °C to 150 °C for 3 h. The yield of functionalization reaction was larger than 60 % and also up to about 90 % for the pyrrole compounds from dodecanamine and 2-amino-1,3-propanediol, respectively. The cycloaddition reaction between the graphene layers and the pyrrole compound, oxidized in two position, is proposed as working hypothesis to account for such efficient functionalization. Raman spectroscopy revealed that the structure of the graphitic substrate remained substantially unaltered, after the reaction. Stable dispersions of HSAG adducts with different PyC were prepared in solvents with different solubility parameters and HRTEM analysis showed the presence of aggregates of only few layers of graphene. Qualitative results of dispersion tests were used to calculate the Hansen sphere for the HSAG adduct with the pyrrole compound based on dodecanamine so to provide a first estimate of its Hansen solubility parameters. This work paves the way for the facile and sustainable modification of the solubility parameters of graphene layers and for the predictive assessment of their compatibility with different environments.

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“…Pyrrole based compounds were prepared through the Paal-Knorr reaction [37,38], by reacting a primary amine with 2,5-HD, as schematically shown in Fig. 1.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Facile and sustainable functionalization of graphene layers with pyrrole compounds

Barbera

Bernardi

Palazzolo

et al. 2017

Pure and Applied Chemistry

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“…Although construction of pyrrole ring has been done by several methods, for example, the Knorr, 22 Paal-Knorr, 23,24 and Hantzsch syntheses. 25 [3 + 2]-cycloadditions, [26][27][28] multicomponent reactions, [29][30][31] and ring contractions 32 or cyclizations, 33-36 a novel and efficient synthetic method for the synthesis of pyrroles is currently being pursued.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Studies of Newly Synthesized Steroidal Pyrroles

Dar¹,

Mir²,

Jan³

et al. 2017

ECB

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“…In recent papers, polymers from serinol have been reported: cyclic carbonates derivatives were converted into polymers through organocatalytic ring opening polymerization [30] and a compound obtained from the reaction of serinol with succinimidyl ester of trimethyl-locked benzoquinone was used to prepare water soluble biodegradable polyester [31]. In this work, serinol chemoselectivity was exploited [32][33][34], preparing SP through the Paal-Knorr reaction [34,35] of serinol (S) with 2,5-hexanedione (HD), performing the reaction in the absence of solvents and catalysts. SP has been defined as a Janus molecule [36], that means a molecule with two faces and, hence, a dual reactivity.…”

Section: Introductionmentioning

confidence: 99%

Polyether from a biobased Janus molecule as surfactant for carbon nanotubes

Barbera¹,

Musto²,

Citterio³

et al. 2016

Express Polym. Lett.

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Abstract.A new polyether (PE) was prepared from a biobased Janus molecule, 2-(2,5-dimethyl-1H-pyrrol-1-yl)-1,3-propanediol (serinol pyrrole, SP). SP was synthesized with very high yield (about 96%) and high atom efficiency (about 80%) by reacting a biosourced molecule, such as serinol, with 2,5-hexanedione in the absence of solvent or catalyst. The reaction of SP with 1,6-dibromohexane led to PE oligomers, that were used as surfactants for multiwalled carbon nanotubes (MWCNT), in ecofriendly polar solvents such as acetone and ethyl acetate. The synergic interaction of aromatic rings and oxyalkylene sequences with the carbon allotrope led to dramatic improvement of surfactant efficiency: only 24% of SP based PE was extracted with ethyl acetate from the adduct with MWCNT, versus 98% of a typical pluronic surfactant. Suspensions of MWCNT-PE adducts in ethyl acetate were stable for months. High resolution transmission electron microscopy revealed a film of oligomers tightly adhered to MWCNT surface.

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Synthese von Thiophen‐ und Pyrrolderivaten

Cited by 451 publications

References 0 publications

Facile and sustainable functionalization of graphene layers with pyrrole compounds

Facile and sustainable functionalization of graphene layers with pyrrole compounds

Spectroscopic Studies of Newly Synthesized Steroidal Pyrroles

Polyether from a biobased Janus molecule as surfactant for carbon nanotubes

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