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  • 1
    Electronic Resource
    Electronic Resource
    Hochreaktive Trialkylsilylierungsreagentien aus Bis(trifluormethansulfonyl)imid - Silylierung von funktionellen Gruppen, alkinen und reaktiven AromatenDie neuartigen Trialkylsilylierungsreagenzien O-(Triisopropylsilyl)-bis-(trifluormethansulfonyl)imid; O-(tert Butyldimethylsilyl)-bis-(trifluormethansulfonyl)-imid und N-(Trimethylsilyl)-bis-(trifluormethansulfonyl)-imid werden demnächst bei Fluka kommerziell erhältlich sein. (1998)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 340 (1998), S. 506-512 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Highly Reactive Trialkylsilylation Reagents Derived from Bis(trifluoromethanesulfonyl)imide - Silylation of Functional Groups, Alkines and Reactive AromaticsThe synthesis of trialylsilyl-bis(trifluormethane-sulfonyl)imides 3 is described. Compounds 3 with bulky trialkylsilyl groups 3a,b only exist in the silatautomeric form 3a′, b′ under usual conditions, 3c in the N-trimethylsilyl structure. Despite of the bulky silyl substituents in 3a′, b′ their reactivity is higher than of trimethylsilyltriflate. Alcohols, carbonyl compounds, nitroalkanes and carboxylic acid esters are silylated in good yields, especially by the more reactive triisopropylsilyl derivative 3b′ in presence of tertiary amines. tert.-Butyl carboxylates and benzylcarboxylates are cleaved. Monosubstituted alkines and electron-rich (hetero) aromatics are carbosilylated in presence of N-ethyl-diisopropylamine.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19983400603
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  • 2
    Electronic Resource
    Electronic Resource
    Reaktionsfähigkeit von Trimethylsilylierungsreagentien (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1718-1721 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactivity of Trimethylsilylation ReagentsThe reactivity of various trimethylsilylation reagents 1 on cyclopentanone (2a) and diisopropyl ketone (2b) has been investigated. Silylation potentials of the reagents 1 are reported.
    Notes: Es wird die Reaktionsfähigkeit einiger Trimethylsilylierungsreagentien 1 gegenüber Cyclopentanon (2a) und Diisopropylketon (2b) untersucht. Silylierungspotentiale der Reagentien 1 werden angegeben.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019801110
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  • 3
    Electronic Resource
    Electronic Resource
    Synthese Cyan-substituierter Heterocyclen mit Tetraethyl-ammoniumcyanid (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 333-341 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Cyano-Substituted Heterocycles by Means of Tetraethylammonium CyanideChloropyrimidines 2, 3 and Chlorquinazolines 9, 10, after conversion into trimethylammonio derivatives 4, 5, 11, 12, react with tetraethylammonium cyanide 1a under very mild conditions to give pyrimidine carbonitriles 6, 7 and quinazoline carbonitriles 13, 14. Direct synthesis of quinoxaline carbonitriles 19 is possible by reaction of chloroquinoxalines 15, 18 with 1a.
    Notes: Die Chlorpyrimidine 2, 3 und Chlorchinazoline 9, 10 können nach Überführung in die Trimethyl-ammonioderivate 4, 5, 11, 12 mit Tetraethylammoniumcyanid (1a) unter sehr milden Bedingungen zu den Pyrimidin- und Chinazolincarbonitrilen 6, 7 bzw. 13, 14 umgesetzt werden. Bei den 2-Chlorchinoxalinen 15, 18 gelingt die direkte Substitution mit 1a zu den Nitrilen 19.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810217
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  • 4
    Electronic Resource
    Electronic Resource
    Synthese von Nitroverbindungen mit Tetraalkylammoniumnitriten (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 628-638 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Nitro Compounds from Tetraalkylammonium NitritesPrimary or secondary bromoalkanes and 2-bromo carbonyl compounds give the nitro derivatives 2, 5 and 7 on reaction with tetraalkylammonium nitrites 1 in dichloromethane or acetonitrile at -50 to 200C. The ratio of nitroalkane and alkyl nitrite (2/3) in the reaction of 1-bromoheptane with the salt 1a in various solvents is investigated. 1,1'-(1,3-Phenylene)dipyrrolidine (6) is a good scavenger for alkyl nitrites.
    Notes: Durch Umsetzung von primären oder sekundären Bromalkanen und 2-Bromcarbonylverbindungen mit Tetraalkylammoniumnitriten 1 in Dichlormethan oder Acetonitril bei -50 bis 200C erhält man die Nitroverbindungen 2, 5 und 7. Das Nitroalkan/Alkylnitrit-Verhältnis (2/3) in verschiedenen Lösungsmitteln wird an der Umsetzung von 1-Bromheptan mit dem Salz 1auntersucht. 1,1'-(1,3-Phenylen)dipyrrolidin (6) eignet sich zum Abfangen der Alkylnitrite 3.
    Additional Material: 9 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919790507
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  • 5
    Electronic Resource
    Electronic Resource
    Sulfosilylierung von Carbonylverbindungen und Trimethylsilylenolethern mit Chlorsulfonsäure-trimethylsilylester (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 39-47 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Sulfosilylation of Carbonyl Compounds and Trimethylsilyl Enol Ethers with Trimethylsilyl ChlorosulfonateAldehydes and Ketones 3 react with trimethylsilyl chlorosulfonate (1a) to yield trimethylsilyl 2-oxosulfonates 5. The course of this sulfosilylation is discussed briefly. The sulfosilylation of trimethylsilyl carboxylates 7 and trimethylsilyl ketene acetals 14 results in formation of 2-(trimethylsiloxysulfonyl)carboxylates 8 and 15.
    Notes: Aldehyde und Ketone 3 sowie Trimethylsilylenolether 12 setzen sich mit Chlorsulfonsäure-trimethylsilylester (1a) zu 2-Oxosulfonsäure-trimethylsilylestern 5 um. Der Ablauf dieser Sulfosilylierung wird kurz diskutiert. Aus Carbonsäure-trimethylsilylestern 7 und Trimethylsilyl-ketenacetalen 14 erhält man mit 1a die Ester 8 und 15 der 2-(Trimethylsiloxysulfonyl)carbonsäuren.
    Additional Material: 6 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840106
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  • 6
    Electronic Resource
    Electronic Resource
    Reaktionen der Trialkylsilyl-trifluormethansulfonate, VI. Synthese von 2-heterosubstituierten O-Alkyl-O-(trimethylsilyl)ketenacetalen und 2-(Trimethylsilyl)carbonsäureestern (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 687-692 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Trialkylsilyl Trifluoromethanesulfonates, VI. - Synthesis of 2-Heterosubstituted O-Alkyl-O-(trimethylsilyl)ketene Acetals and 2-(Trimethylsilyl)carboxylatesOrganooxy- and (alkylthio)ethanoic acid esters 2 are silylated by trimethylsilyl triflate (1) in the presence of triethylamine to yield mixtures of ketene acetals 3 and 2-(trimethylsilyl)ethanoates 4. The product distributions 3/4 are governed by the ester groups and the substituents in α position. Cyclic derivatives of 2-hydroxycarboxylic acids 7,9 are silylated by 1/triethylamine to give the ketene acetals 8, 10. From N-protected glycine methyl esters 11, 12 the ketene acetals 13, 15 are obtained in the reaction with 1/triethylamine.
    Notes: Durch Silylierung von Organooxy- und (Alkylthio)essigestern 2 mit Trimethylsilyltriflat (1) in Gegenwart von Triethylamin erhält man Gemische aus Ketenacetalen 3 und 2-(Trimethylsilyl)essigestern 4. Die Produktverteilung 3/4 wird durch die Estergruppen sowie die α-Substituenten in den Estern 2 gesteuert. Cyclische Derivate der 2-Hydroxycarbonsäuren 7, 9 werden durch 1/Triethylamin in die Ketenacetale 8, 10 übergeführt. N-geschützte Glycin-methylester 11, 12 ergeben bei Umsetzung mit 1/Triethylamin die Ketenacetale 13, 15.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870809
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  • 7
    Electronic Resource
    Electronic Resource
    Reaktionen der Trialkylsilyl-trifluormethansulfonate, IX. Elektrophile Silylierung elektronenreicher Alkene (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 745-750 
    Details
    ISSN: 0170-2041
    Keywords: Ketene acetals, 2-(trimethylsilyl)- ; Trialkylsilyl trifluoromethanesulfonates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of Trialkylsilyl Trifluoromethanesulfonates, IX.  -  Electrophilic Silylation of Electron-Rich AlkenesKetene O,O-, O,S-, and O,N-acetals 1, 7, and 9 are converted into the C-silylated derivatives 4, 8, and 11, respectively, by reaction with trimethylsilyl triflate (2a)/tertiary amine or sodium hydride. The ambident character of the ketene O,O-acetals 1 in the silylation with 2a is studied.
    Additional Material: 9 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001140
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  • 8
    Electronic Resource
    Electronic Resource
    Reaktionen der Trialkylsilyl-trifluormethansulfonate, IV. 1,3-Trialkylsiloxy-Verschiebung - eine neuartige Umlagerungsreaktion bei der Silylierung von Nitroalkanen (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 428-437 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Trialkylsilyl Trifluoromethanesulfonates, IV.  -  1,3-Trialkylsiloxy Shift - a New Rearrangement Reaction During the Silylation of NitroalkanesNitroalkanes 1 with C — H bonds in β-position react with two-fold molar amounts of trialkylsilyl triflates 2 in the presence of triethylamine to yield 2-(trialkylsiloxy)oxime O-trialkylsilyl ethers 5 by 1,3-trialkylsiloxy shift. Oxime ethers 5 are also obtained by reaction of aci-nitroalkane trialkylsilyl esters 3 with molar quantities of silylation reagents 2. The dependence of the reaction from the nature of the nitroalkane 1 and the alkyl groups in the silylation reagent 2 is investigated.
    Notes: Nitroalkane 1 mit C—H-Funktionen in β-Position ergeben bei der Silylierung mit doppelt molaren Mengen Trialkylsilyl-triflaten 2 in Gegenwart von Triethylamin unter 1,3-Trialkylsiloxy-Verschiebung 2-(Trialkylsiloxy)oxim-O-trialkylsilylether 5. Die Oximether 5 resultieren ebenso aus der Umsetzung von aci-Nitroalkan-trialkylsilylestern 3 mit molaren Mengen Silylierungsagens 2. Die Abhängigkeit der Reaktion von der Struktur der Nitroalkane 1 und der Raumerfüllung der Alkylreste am Silylierungsagens 2 wird untersucht.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860303
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  • 9
    Electronic Resource
    Electronic Resource
    Reaktionen der Trialkylsilyl-trifluormethansulfonate, I. Synthese von Trialkylsilyl-Enolethern (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 1643-1657 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Trialkylsilyl Trifluoromethanesulfonates, I. - Synthesis of Trialkylsilyl Enol EthersThe reactions of the ketones 2, 2-bromoketones 6, α,β-unsaturated ketones 8, 1,2-diketones, and aliphatic aldehydes 20 with trialkylsilyl triflates 1 in the presence of triethylamine (4) at room temperature yield the silyl enol ethers 3, 7, 9, 11, and 21. The silylation of the unsymmetrical ketones 12 with 1a/4 runs regioselectively in the thermodynamical sense using 1a/12 in excess and yields the enol ethers 13t. The course of this reaction is discussed briefly.
    Notes: Die Ketone 2, 2-Bromketone 6, α,β-ungesättigte Ketone 8, 1,2-Diketone 10 und aliphatische Aldehyde 20 setzen sich mit Trialkyisilyl-triflaten 1 in Gegenwart von Triethylamin (4) bei Raum-temperatur zu den Silylenolethern 3, 7, 9, 11 und 21 um. Die Silylierung unsymmetrischer Ketone 12 mit 1a/4 verläuft mit überschüssigem 1a und 12 regioselektiv im thermodynamischen Sinn zu den Enolethern 13t. Der Reaktionsablauf wird kurz diskutiert.
    Additional Material: 9 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810913
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  • 10
    Electronic Resource
    Electronic Resource
    Sulfosilylierung von Aromaten mit Chlorsulfonsäure-trimethylsilylester (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 282-297 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Sulfosilylation of Aromatic Hydrocarbons by Trimethylsilyl ChlorosulfonateAromatic hydrocarbons 2, 6, 8, 9, 13, 16, 18, 19, 22 react with trimethylsilyl chlorosulfonate (1) to give trimethylsilyl arenesulfonates 5, 7, 11, 12, 15, 23 or sulfonic acids 17, 20, 21. If trimethylsilyl sulfonates are obtained, working up of the sulfonation mixtures is possible by distillation. By hydrohalogenolysis of trimethylsilyl sulfonates 5 at 0-5°C anhydrous sulfonic acids 3 result. The pathways to diphenylsulfone (25a) in the reaction of benzene (2a) with 1 were investigated. In this connection we succeeded in synthesizing benzenepyrosulfonic acid (28) and trimethylsilyl benzenepyrosulfonate (29).
    Notes: Durch Umsetzung der Aromaten 2, 6, 8, 9, 13, 16, 18, 19, 22 mit Chlorsulfonsäure-trimethylsilylester (1) erhält man die Arensulfonsäure-trimethylsilylester 5, 7, 11, 12, 15, 23 bzw. Sulfonsäuren 17, 20, 21. Die Aufarbeitung der Sulfonierungsgemische erfolgt, wenn Silylester entstehen, destillativ. Aus der Hydrohalogenolyse der Trimethylsilylester 5 bei 0-5°C resultieren die wasserfreien Sulfonsäuren 3. Am Beispiel der Reaktion von Benzol (2a) mit 1 werden die Möglichkeiten der Bildung von Diphenylsulfon (25a) untersucht. In diesem Zusammenhang gelang die Synthese von Benzolpyrosulfonsäure (28) und Benzolpyrosulfonsäure-trimethylsilylester (29).
    Additional Material: 11 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820212
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