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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
    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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  • 3
    Electronic Resource
    Electronic Resource
    Reaktionen der Trialkylsilyl-trifluormethansulfonate, II. Synthese von O-Alkyl-O-(trialkylsilyl)ketenacetalen und 2-(Trialkylsilyl)carbonsäureestern (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 816-834 
    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, II. - Synthesis of O-Alkyl-O-(trialkylsily1)ketene Acetals and 2-(Trialkylsilyl)carboxylatesAlkyl carboxylates 2 are silylated by trialkylsilyl triflates 1 in the presence of triethylamine (3) to yield ketene acetals 4. In reactions of the esters 6 mixtures of ketene acetals 7 and at the α-carbon silylated esters 8 are obtained. Ethanoic acid esters and lactones are doubly silylated to give the products 11, 12, and 15, respectively. Under suitable conditions silylation of the esters 10 gives rise to the 2-trimethylsilylethanoic acid esters 13. The thermodynamically more stable products are obtained. Product distributions depend on the structure of the esters and the silylating agents 1.
    Notes: Durch Silylierung mit Trialkylsilyltriflaten 1 in Gegenwart von Triethylamin (3) erhält man aus Carbonsäureestern 2 die Ketenacetale 4, die Ester 6 ergeben Gemische aus Ketenacetalen 7 und am α-Kohlenstoffatom silylierten Estern 8. Ethansäureester 10 und Lactone 14 werden durch 1/3 zweifach zu den Produkten 11, 12 bzw. 15 silyliert. Unter geeigneten Bedingungen können 2-(Trimethylsilyl)ethansäureester 13 aus den Estern 10 gewonnen werden. Es resultieren die thermodynamisch stabilen Produkte. Die Abhängigkeit der Produktverteilung von der Struktur der Reaktionspartner wird diskutiert.
    Additional Material: 10 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830508
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  • 4
    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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  • 5
    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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  • 6
    Electronic Resource
    Electronic Resource
    Reaktionen der Trialkylsilyl-trifluormethansulfonate, XI. Synthese von Derivaten der α-Ketocarbonsäuren aus 2-O-funktionell substituierten Trimethylsilylketenacetalen (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 607-613 
    Details
    ISSN: 0170-2041
    Keywords: 1,3-Dioxolanes ; 1,3-Oxazolidines ; α-Oxocarboxylic acids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of Trialkylsilyl Trifluoromethanesulfonates XI.  -  Synthesis of α-Oxocarboxylic Acid Derivatives from 2-O-Functionalized Trimethylsilyl Ketene AcetalsThe cyclic ketene acetals 3, 5 are prepared from the dioxolanone 2 resp. the oxazolidinediones 4 by silylation with trimethylsilyl triflate (1)/triethylamine. In an aldol addition/Peterson olefination reaction catalysed by 1 the ketene acetals 3, 5 yield the (E/Z)-benzylidene derivatives 7, 12, 13 in reaction with aromatic aldehydes 6. In a side reaction the α-(trimethylsilyl)benzylidene derivatives 8 are formed from 3 and 6. Compounds 7 can be hydrolysed to yield α-ketocarboxylic acids 14. The latter are also obtained via β-elimination of trimethylsilanol from 2,3-bis(trimethylsiloxy)carboxylic acid esters 15 with trifluoroacetic acid anhydride/DMAP/pyridine.
    Additional Material: 11 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201104
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  • 7
    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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  • 8
    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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  • 9
    Electronic Resource
    Electronic Resource
    Reaktionen der Trialkylsilyl-trifluormethansulfonate, III. Synthese von 1,3-Bis(trimethylsiloxy)-1,3-dienen und in 4-Stellung silylierten 3-Trimethylsiloxy-2-butensäureestern (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 2352-2362 
    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, III.  -  Synthesis of 1,3-Bis(trimethylsiloxy)-1,3-dienes and 3-Trimethylsiloxy-2-butenoates Silylated in Position 4Bis(trimethylsiloxy)-1,3-dienes 5a  -  n are obtained by reaction of 1,3-dicarbonyl compounds 1 with trimethylsilyl trifuoromethanesulfonate (2) in the presence of triethylamine (3). The silyl enol ether 8 is silylated by 2/3 to yield 1,3-bis(trimethylsiloxy)-1,3-butadiene (5o). Depending on the conditions, alkyl 3-oxobutanoates 12 react with 2/3 to give the γ-silylated alkyl 3-trimethylsiloxy-2-butenoates 15 or 16.
    Notes: Durch Umsetzung der 1,3-Dicarbonylverbindungen 1 mit Trimethylsilyltriflat (2) in Gegenwart von Triethylamin (3) erhält man die Bis(trimethylsiloxy)-1,3-diene 5a - n. 1,3-Bis(trimethylsiloxy)-1,3-butadien (5o) entsteht bei der Silylierung des Silylenolethers 8 mit 2/3. 3-Oxobutansäure-alkylester 12 werden von 2/3 je nach Reaktionsbedingungen in die γ-silylierten 3-(Trimethylsiloxy)-2-butensäureester 15 oder 16 übergeführt.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519851206
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  • 10
    Electronic Resource
    Electronic Resource
    Reaktionen der Trialkylsilyl-trifluormethansulfonate, V. Synthese und Reaktionen von N,N-Bis(trialkylsiloxy)-1-alken-1-aminen (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 1456-1465 
    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, V. - Synthesis and Reactions of N,N-Bis(trialkylsiloxy)-1-alken-1-aminesNitroalkanes 1 react with trialkylsilyl triflates 2 in the presence of triethylamine to yield N,N-bis(trialkylsiloxy)-1-alken-1-amines (nitrosoalkene acetals) 4, which are rearranged to give 2-(trialkylsiloxy)oxime O-trialkylsilyl ethers 6 by heating or by Lewis acids. 2-Amino-aldoxime O-trialkylsilyl ethers 8 or 2-aminoaldoximes 9 are obtained by reaction of amines 7 with the acetals 4.
    Notes: Nitroalkane 1 reagieren mit Trialkylsilyl-triflaten 2 in Gegenwart von Triethylamin zu N,N-Bis(trialkylsiloxy)-1-alken-1-aminen (Nitrosoalken-acetale) 4, die thermisch oder durch Lewis-Säuren in 2-(Trialkylsiloxy)oxim-O-trialkylsilylether 6 umgelagert werden. Durch Umsetzung der Acetale 4 mit Aminen 7 erhält man 2-Aminoaldoxim-O-trialkylsilylether 8 bzw. 2-Aminoaldoxime 9.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860817
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