Cyanoalkynes: Magic wands for the preparation of novel aromatic compounds

Hopf, Henning; Witulski, B.

doi:10.1351/pac199365010047

Cited by 29 publications

(12 citation statements)

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“…I have always remained very thankful to both of them, as I have been to the late Karsten Krohn, who was my mentor at Paderborn in 1995. Back in 1989 already, Henning Hopf had told me that his group had made a doubly benzoannelated triquinacene,[160] but it was only in 2012 that I received an e‐mail telling me that Georgios Markopoulos, one of his doctoral students, had possibly obtained a hydrocarbon that resembles the parent tribenzotriquinacene 57 (R = H). Upon treatment of a mixture of the stereoisomeric 2‐benzylidene‐1,3‐diphenylpropane‐1,3‐diols ( 67 ) with acid catalysts, they had obtained very high‐melting‐point crystals that had a remarkably simple 1 H NMR spectrum.…”

Section: The Tribenzotriquinacene Storymentioning

confidence: 99%

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

Kuck

2015

The Chemical Record

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Detailed insights gained from our research into the gas-phase chemistry of ionized and protonated diphenylalkanes and their congeners, obtained by extended synthesis of isotopically labeled model compounds and mass spectrometry, are presented and merged with those acquired during our development of a new family of polycyclic hydrocarbons, the centropolyindanes. Aside from a Personal Account that describes "two scientific lives in one", it is demonstrated, on the one hand, how our understanding of organic chemistry can help to shed light on the details of mass spectrometric fragmentation and to unravel, in a more fundamental way, the unimolecular reactivity of gaseous ions. On the other hand, it is shown how unexpected reactivity of related ions in solution, being subject to the very same fundamentals of organic chemistry, can lead to the construction of novel and, in part, unique three-dimensional polycyclic structures that may contribute to future research in material science. Two such apparently independent fields of organic chemistry may be seen as joint contributions of the art of science.

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Section: The Tribenzotriquinacene Storymentioning

confidence: 99%

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

Kuck

2015

The Chemical Record

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“…Chemoselective ruthenium-catalyzed cycloadditions leading to cyanoarenes (50) and 2-alkynylpyridines (51). which clearly indicated that the neutral Ru-complex is responsible for the formation of cyanobenzenes, whereas, cationic Rucomplex generated in-situ plays a crucial role for the 2alkynylpyridines formation.…”

Section: Scheme 25mentioning

confidence: 97%

“…They assumed that cyanoacetylene dimerizes to 1,2-dicyanocyclo butadiene and synthesized various novel aromatic and heteroaromatic compounds by trapping it with various aromatic and heteroaromatic dienes (Scheme 27). [51] In 1968, Sasaki and co-worker described the 1,3-dipolar cycloaddition between cyanoacetylene and aromatic nitrile oxide. [52] In the following year, they documented the synthesis of cyclobutene ring (54) by the reaction of diethyl-aminocyanoacetylene (53) with hydrogen chloride gas (Scheme 28).…”

Section: Transition Metal-free Synthesis Of Various Carbo-/heterocyclmentioning

confidence: 99%

Syntheses and Applications of 2‐Alkynylnitriles

2019

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2-Alkynylnitriles are a distinguished class of molecules known to play a pivotal role in the construction of a plethora of carbo-/heterocyclic compounds of biological and pharmaceutical importance. These molecules have been exploited as hydrolytically stable irreversible labels for cysteine tagging. In addition, they also form an important homologous series of complex interstellar molecules identi-fied by radioastronomy. Therefore, in this Minireview, we highlight the numerous transformations and diverse reactions carried out with these substrates. Different reactions including nucleophilic additions and various carbo-/heterocycles formation are the prime focal areas of this article. Mechanistic aspects for certain reactions have also been delineated. Scheme 1. Synthesis of 3-phenyl-2-propynylnitrile (3) using cyanogen bromide as cyanating agent.Scheme 2. Synthesis of various 2-alkynylnitrile derivatives employing phenyl cyanate (4) as cyanating agent.

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“…Reduction at the vinylidene alpha carbon C(1), which is consistent with the composition of the LUMO, is more in keeping with the spectroelectrochemical results. vinylidenes to alkynes at half-sandwich ruthenium and iron centres [37], future work from this group will address the potential to use a combination of these chemistries to provide a simple ruthenium-catalysed route to cyanoalkynes [108] from [9]BF 4 and terminal alkynes and to make these useful reagents readily available.…”

Section: Electronic Structure Calculations and Spectroelectrochemistrymentioning

confidence: 99%

The synthesis, molecular and electronic structure of cyanovinylidene complexes

Long¹,

Brown²,

Man³

et al. 2012

Inorganica Chimica Acta

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Cyanoalkynes: Magic wands for the preparation of novel aromatic compounds

Abstract: Abstract

Cited by 29 publications

References 0 publications

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

Syntheses and Applications of 2‐Alkynylnitriles

The synthesis, molecular and electronic structure of cyanovinylidene complexes

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