Ueber ein Condensationsproduct von Pyrrol mit Aceton

Baeyer, Adolf

doi:10.1002/cber.188601902121

Cited by 290 publications

(181 citation statements)

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“…It may be viewed as a singular twist of fate that a molecule Baeyer reported soon after publishing his strain theory actually contained a 16-membered ring. [72] Octamethylcalix [4]pyrrole, [73] as the compound is now known, could well be the first synthetic macrocycle isolated in pure form.…”

Section: Conformation Of Porphyrinoidsmentioning

confidence: 99%

Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids

2011

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The aromatic character of porphyrins, which has significant chemical and biological consequences, can be substantially altered by judicious modifications of the parent ring system. Expansion of the macrocycle, which is achieved by introducing additional subunits, usually increases the so-called free curvature of the ring, leading to larger angular strain. This strain is reduced by a variety of conformational changes, most notably by subunit inversion and p surface twisting. The latter effect creates a particularly convenient access to Möbius aromatic molecules, whose properties, predicted over 40 years ago, are of considerable theoretical importance. The conformational processes occurring in porphyrin analogues are often coupled to other chemical phenomena, and can thus be exploited as a means of constructing functional molecular devices. In this Review, the structural chemistry of porphyrinoids is discussed in the context of their conformational dynamics and p-electron conjugation.

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Section: Conformation Of Porphyrinoidsmentioning

confidence: 99%

Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids

2011

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“…Among the most popular anion receptors, a very interesting example is meso-octamethylporphyrinogen, more commonly known as meso-octamethylcalix [4]pyrrole (CP). This receptor was originally discovered by Baeyer 17 in 1886 but only recently its anion binding properties were recognized. 18 The main advantages of its use in anion recognition and sensing are its easy and quick synthesis, [19][20][21][22][23] associated with the fact that functionalized anion sensors can be designed by means of the integration of the calix [4]pyrrole with different signaling subunits.…”

Section: Introductionmentioning

confidence: 99%

Anionic chromogenic chemosensors highly selective for fluoride or cyanide based on 4-(4-Nitrobenzylideneamine)phenol

Nicoleti

Marini

Zimmermann

et al. 2012

J. Braz. Chem. Soc.

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4-(4-Nitrobenzylideneamine)phenol was used in two strategies allowing the highly selective detection of F -and CN -. Firstly, the compound in acetonitrile acts as a chromogenic chemosensor based on the idea that more basic anions cause its deprotonation (colorless solution), generating a colored solution containing phenolate. The discrimination of CN -over F -was obtained by adding 1.4% water to acetonitrile: water preferentially solvates F -, leaving the CN -free to deprotonate the compound. Another strategy involved an assay comprised of the competition between phenolate dye and the analyte for calix [4]pyrrole in acetonitrile, a receptor highly selective for F -. Phenolate and calix[4]pyrrole form a hydrogen-bonded complex, which changes the color of the medium. On the addition of various anions, only F -was able to restore the original color corresponding to phenolate in solution due to the fact that the anion dislodges phenolate from the complexation site.

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“…Various attempts have been made for the development of milder methods for the synthesis of porphyrins [20][21][22], N-C isomerization [23,24] and higher homologues of porphyrins [25]. The meso-octamethylcalix [4]pyrrole 3a has been prepared by condensation of pyrrole with acetone in the presence of aqueous hydrochloric acid or methanesulfonic acid in methanol [26,27]. The reaction of pyrrole and acetone in the presence of trifluoroacetic acid in ethanol gave meso-octamethylcalix [4]pyrrole (3a) and the N-confused octamethylcalix [4]pyrrole (4b) [28].…”

Section: Introductionmentioning

confidence: 99%

Syntheses of Calix[4]Pyrroles by Amberlyst-15 Catalyzed Cyclocondensations of Pyrrole with Selected Ketones

2007

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Ueber ein Condensationsproduct von Pyrrol mit Aceton

Cited by 290 publications

References 0 publications

Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids

Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids

Anionic chromogenic chemosensors highly selective for fluoride or cyanide based on 4-(4-Nitrobenzylideneamine)phenol

Syntheses of Calix[4]Pyrroles by Amberlyst-15 Catalyzed Cyclocondensations of Pyrrole with Selected Ketones

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