Synthese eines stabilen Alkylidenketenimins und eines Alkylidenthioketens

Bestmann, Hans Jürgen; Schmid, Günter; Sandmeier, D.

doi:10.1002/ange.19750870105

Cited by 17 publications

(6 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ylide 1 19 and the pyrazolones 16 20 were prepared by the literature methods, all other starting compounds were purchased from Aldrich and used as such without further purification.…”

Section: Methodsmentioning

confidence: 99%

Selective C-acylation of CH-active dicarbonyl compounds with ketenylidenetriphenylphosphorane: syntheses and structures of 3-phosphoranylideneacyltetronic acids, 3-phosphoranylideneacyl-4-oxocoumarins, and 4-phosphoranylideneacylpyrazol-5-ones

Schobert

Siegfried

Nieuwenhuyzen

et al. 2000

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

“…Ylide 1 19 and the pyrazolones 16 20 were prepared by the literature methods, all other starting compounds were purchased from Aldrich and used as such without further purification.…”

Section: Methodsmentioning

confidence: 99%

Selective C-acylation of CH-active dicarbonyl compounds with ketenylidenetriphenylphosphorane: syntheses and structures of 3-phosphoranylideneacyltetronic acids, 3-phosphoranylideneacyl-4-oxocoumarins, and 4-phosphoranylideneacylpyrazol-5-ones

Schobert

Siegfried

Nieuwenhuyzen

et al. 2000

J. Chem. Soc., Perkin Trans. 1

View full text Add to dashboard Cite

“…A solution of 1-trimethylsilyl-1H-imidazole (1) (0.14 g, 0.001 mol) in dry toluene (20 mL) was added to a solution of (N-phenyliminovinylidene) triphenylphosphorane (2a) 21 (0.37 g, 0.001 mol) or (2-oxovinylidene) triphenylphosphorane (2b) 22 (0.30 g, 0.001 mol) in toluene (20 mL). The reaction mixture was refluxed for 5 h when using 2a and for 7 h when using 2b.…”

Section: Reaction Of 1-trimethylsilyl-1h-imidazole (1) With Active Phosphacumulene Ylides 2a and 2bmentioning

confidence: 99%

Chemistry of Phosphorus Ylides: Part 44 Reaction of 1-Trimethylsilyl-1H-Imidazole with Phosphorus Reagents. A Convenient Synthesis of Phosphorus Silyl Imidazoles

El‐Hussieny

Abd‐El‐Maksoud

Maigali

et al. 2016

Journal of Chemical Research

View full text Add to dashboard Cite

Trimethylsilylimidazoles have received much attention because of their synthetic and application challenges. 1,2 Moreover, the trimethylsilyl group is characterised by chemical inertness and a large molecular volume, which makes it useful in a number of applications. [3][4][5] Trimethylsilylimidazoles are used as silyl protecting and derivatisation reagents, 6,7 reducing agents, 8 in cross-coupling chemistry 9 and to stabilise α-carbanions and β-carbocations. 9 Previously we studied the reactions of the active phosphacumulenes, phosphallenes, stabilised phosphonium ylides, Lawesson and Japanese reagents to prepare new heterocyclic and homocyclic compounds containing phosphorus moieties of industrial and biological interest. [10][11][12][13][14][15][16][17][18][19] Results and discussionWe now report the reaction of 1-trimethylsilyl-1H-imidazole (1) with (N-phenyliminovinylidene)triphenylphosphorane (2a), (2-oxovinylidene)triphenylphosphorane (2b), hexaphenylcarbodiphosphorane (5), Lawesson's reagent (8a) and Japanese reagent 9a (Schemes 1-4). The phosphacumulene ylides (2a and 2b) can each be described by the resonance structures 2A and 2B (Scheme 1). Accordingly, treatment of 1 with 1 equiv. of 2a in dry toluene led to the formation of imidazolesilylphosphoranylidene aniline 3a. When the reaction was performed in hot THF and the product was chromatographed on silica gel, the new compound imidazolephosphoranylidene aniline 4a was isolated. Adduct 3a was formed by nucleophilic attack of 2a on 1 and fast exchange

show abstract

“…A mixture of triphenyl(N-phenyliminovinylidene)phosphorane (2a) 44 (377 mg, 1 mmol) in 20 mL of dry THF, was added dropwise with stirring at room temperature, to a solution of 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one (1) (203 mg, 1 mmol) in 20 mL of dry THF. The reaction mixture was stirred for 6 h during which the colour changed from yellow to dark brown with the progress of the reaction which was monitored by TLC.…”

Section: Reaction Of Triphenyl(n-phenyliminovinylidene)phosphorane (2a) With (4-amino-15-dimethyl-2-phenyl-12-dihydro Pyrazol-3-one) (1)mentioning

confidence: 99%

Chemistry of Phosphorus Ylides: Part 41 Synthesis of Antimicrobial Agents from the Reaction of Aminoantipyrine, Coumarin- and Quinoline-carbaldehyde with Phosphacumulene and Phosphaallene Ylides

Maigali

Abd‐El‐Maksoud

El‐Hussieny

et al. 2014

Journal of Chemical Research

View full text Add to dashboard Cite

Pyrrolo-pyrazoles were obtained from the reaction between phosphacumulenes and aminoantipyrine, while the reaction with the phosphaallene (hexaphenylcarbodiphosphorane ylide) afforded the azaphosphole and pyrazolo-phosphanylidene. The aminocoumarin carbaldehyde gave the chromeno-phosphanylidene and the chromeno-pyridinone, when it was allowed to react with phosphacumulenes. The reaction of chloroquinoline carbaldehyde with the phosphacumulenes, gave chloroquinoline phosphanylidenecyclobutane, while the reaction with phosphaallene resulted in the formation of oxaphosphetane, phosphanylidene ethenyl-and oxaphosphetyl-quinoline. The structure of cyclobutanedione was confirmed by X-ray crystallography. The antimicrobial activity of the new compounds is also reported.

show abstract

Synthese eines stabilen Alkylidenketenimins und eines Alkylidenthioketens

Cited by 17 publications

References 3 publications

Selective C-acylation of CH-active dicarbonyl compounds with ketenylidenetriphenylphosphorane: syntheses and structures of 3-phosphoranylideneacyltetronic acids, 3-phosphoranylideneacyl-4-oxocoumarins, and 4-phosphoranylideneacylpyrazol-5-ones

Selective C-acylation of CH-active dicarbonyl compounds with ketenylidenetriphenylphosphorane: syntheses and structures of 3-phosphoranylideneacyltetronic acids, 3-phosphoranylideneacyl-4-oxocoumarins, and 4-phosphoranylideneacylpyrazol-5-ones

Chemistry of Phosphorus Ylides: Part 44 Reaction of 1-Trimethylsilyl-1H-Imidazole with Phosphorus Reagents. A Convenient Synthesis of Phosphorus Silyl Imidazoles

Chemistry of Phosphorus Ylides: Part 41 Synthesis of Antimicrobial Agents from the Reaction of Aminoantipyrine, Coumarin- and Quinoline-carbaldehyde with Phosphacumulene and Phosphaallene Ylides

Contact Info

Product

Resources

About