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  • Organic Chemistry  (17)
  • Asymmetric synthesis  (2)
  • Electroreduction  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Elektroreduktion organischer Verbindungen, 16. Elektroreduktion von ω-Halogenalkandithiosäure-methylestern (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 1733-1737 
    Details
    ISSN: 0009-2940
    Keywords: Dithiolactones ; Electroreduction ; Haloalkanedithioates ; Thioacetals, semicyclic ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Intramolecular cyclization occurs on electroreduction of the methyl -haloalkanedithioates 1 in methanol. The expected semicyclic thioacetals 2 are formed according to an ECEH mechanism. The biheterocycles 12 result from dimerization of intermediate radicals whereas the semicyclic ketene dithio-acetals 13 are formed by non-electrochemical processes. The 2-(methylthio)thiolanes 2 a and 16 are obtained with much higher yields and better selectivity by co-electroreduction of the -dithio-lactones 15 in the presence of dimethyl sulfate.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230825
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  • 2
    Electronic Resource
    Electronic Resource
    The He(Iα) Photoelectron Spectra of Substituted 1,2-Dithietes (1983)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 66 (1983), S. 801-808 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The He(Iα) photoelectron (PE.) spectra of a series of substituted 1,2-dithietes have been recorded and assigned with respect to the orbital sequence derived from an STO-3G model calculation and by correlation with the PE. spectra of related compounds. The results provide additional support for the presence of a closed, four-membered ring moiety in all the 1,2-dithietes investigated. In all cases the two highest occupied molecular orbitals are b2(π)= HOMO, a2(π), with exception of 3,4-bis(trifluoromethyl)-1,2-dithiete where the sequence b2(π), a2(π) or a2(π), b2(π) is uncertain.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19830660312
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  • 3
    Electronic Resource
    Electronic Resource
    Elektroreduktion organischer Verbindungen, 19 Bildung benzoanellierter Schwefelheterocyclen durch intramolekulare kathodische Cyclisierung von Dithiocarbonsäureestern (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 127-141 
    Details
    ISSN: 0009-2940
    Keywords: Dithiopivaloates, S-aryl, S-benzyl ; Electroreduction ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Electroreduction of Organic Compounds, 19.  -  Formation of Benzoanellated Sulfur Heterocycles by Intramolecular Cathodic Cyclization of Dithiocarboxylic EstersCathodic reduction of aryl (3) and benzyl (5) dithiopivaloates and related dithioesters with leaving groups at the benzene ring or a side chain yield the sulfur heterocycles 23, 30 - 32, and 34 depending on the nature of the starting material and the reaction conditions. In case of the α-oxo-dithioester 22, thioindigo (44) is formed.  -  The corresponding thioamides 14, 16, and 18 show a strong tendency to reductive dehalogenation but the S,N-heterocycles 38 and 39 are also formed in minor amounts.  -  The formation of the rearranged products 29 - 32, and 34 is discussed in terms of C,S-splitting in the primarily formed radical anion and subsequent C,C-coupling of the fragments and follow-up reactions.
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250122
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  • 4
    Electronic Resource
    Electronic Resource
    Formation of δ-Sultines (1,2-Oxathiane 2-Oxides) from Thiolane 1-Oxides (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 943-947 
    Details
    ISSN: 1434-193X
    Keywords: Thiolane 1-oxides ; Oxidations ; δ-Sultines ; [Bis(trifluoroacetoxy)iodo]benzene ; Asymmetric synthesis ; Carbanions ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -2-(Alkylthio)-2-benzylthiolane 1-oxides (1a, b) and 2-(alkylthio)-2-(α-hydroxybenzyl)thiolane 1-oxides (1c, d) are oxidized with [bis(trifluoroacetoxy)iodo]benzene (PIFA). Under ring enlargement the corresponding cyclic sulfinate esters (δ-sultines) 2 are formed. Only (1R*,2S*)-1b is reactive whereas (1R*,2R*)-1b is not attacked. This observation is explained with the formation of a cyclic intermediate 3.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Electroreduction of organic compounds. 31. Electroreduction of 2- and 3-Chlorodibenzofuran in Deuterated Methanol (1998)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 340 (1998), S. 430-436 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The cathodic reduction of dibenzofuran (2), 2-chlorodibenzofuran (4), and 3-chlorodibenzofuran (1) in deuterated methanol is investigated. The Birch-type reduction product 1,4-dibenzofuran (3) is formed from 1 via 2, whereas 2-chloro-1,4-dihydrodibenzofuran (5) is obtained as by-product besides 3 from 4 as starting compound. Deuterium is only incorporated into the reduction products if CH3OD or CD3OD but not if CD3OH are used. This observation is strongly indicative of a polar mechanism involving protonation rather than a radical mechanism with hydrogen atom abstraction to be operative.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19983400505
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  • 6
    Electronic Resource
    Electronic Resource
    Reaction of the Carbanions of 2-(Alkylthio)thiolane 1-Oxides with Oxiranes (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1481-1488 
    Details
    ISSN: 1434-193X
    Keywords: Thiolane 1-oxides ; Carbanions ; Oxiranes ; Asymmetric synthesis ; X-ray structure ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Carbanions of the 2-(alkylthio)thiolane 1-oxides 1 and 2 are generated and subjected to reaction with the epoxides 3-5. The resulting carbinols 6-11 are formed with high α diastereoselectivity, which is explained by a stabilization of the trans configuration of the carbanions in the activated complex. A minor γ stereoselectivity is also observed in case of the reactions with 4 and 5. The pure enantiomers (1S,2S,2′S)-9a and (1R,2R,2′S)-11b were obtained from 2 and (S)-4 or (R)-5, respectively, and their configurations were proved by X-ray structural analyses.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Darstellung von Benzo[c]thiophenen nach neueren Varianten der Hinsberg-Reaktion (1991)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 333 (1991), S. 889-893 
    Details
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Preparation of Benzo[c]thiophenes Using a Modified Hinsberg-ReactionWhereas the tetrahydrobenzo[c]thiophenes 3 and 6 are easily obtained from 1 and 2 or 4 their dehydrogenation (i. e. aromatization) is difficult and the yields are low. However, the method allows to prepare hitherto unknown benzo[c]thiophenes with special substituents in the 1,3-positions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19913330611
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  • 8
    Electronic Resource
    Electronic Resource
    Darstellung von Diaryl- und Aryl-tert-butyl-α-thioxoketonen (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 10-19 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation of Diaryl and Aryl tert-Butyl α-ThioxoketonesThe preparation of the α-haloketones 6, 13-16, 19, and 20 is reported. 13 or its precursor, the acyloin 9, respectively, is conveniently obtained by a Seebach synthesis.  -  Reaction of the haloketones with tetraethylammonium thiosulfate (21) yields the Bunte salts 22-27 which form the thioketones 28-33 on cleavage with aqueous alkali. 29 is stable as a crystalline, blue monomer in contrast with other aromatic α-thioxoketones. This ist also true for the aromatic-aliphatic derivatives 30 and 31 as well as their isomers 32 and 33 which do not dimerize.
    Notes: Die Darstellung der α-Halogenketone 6, 13-16, 19 und 20 wird beschrieben. 13, bzw. seine Vorstufe 9, ist am besten durch eine Seebach-Synthese zugänglich.  -  Durch Umsetzung mit Tetraethylammonium-thiosulfat (21) erhält man aus den Halogenketonen die Bunte-Salze 22-27, die nach Spaltung mit Alkali die Thioketone 28-33 liefern. 29 ist im Gegensatz zu anderen aromatischen α-Thioxoketonen als kristallisiertes blaues Monomeres beständig. Auch die aromatisch-aliphatischen Vertreter 30 und 31 sowie ihre Isomeren 32 und 33 dimerisieren nicht.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810104
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  • 9
    Electronic Resource
    Electronic Resource
    Elektroreduktion organischer Verbindungen, 2. Darstellung von Dithioacetalen durch alkylierende Elektroreduktion von Dithiocarbonsäureestern (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 472-480 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Electroreduction of Organic Compounds, 21).  -  Preparation of Dithioacetals by Electroreductive Alkylation of Alkyl DithiocarboxylatesAlkyl dithiobenzoates 1 and O-methyl thiobenzoate (7) yield the benzaldehyde dithioacetals 2 or monothioacetals 8, respectively, by electroreduction in the presence of alkyl halides. The S-acylal 3b is formed from ethyl dithiobenzoate 1b in the presence of acetic anhydride.  -  The dithioacetals 5 and the ketene dithioacetals 6 are obtained by co-electroreduction of methyl dithiopropionate (4) with alkyl halides.  -  Conclusions about the reaction mechanism are drawn from voltammetric measurements.
    Notes: Dithiobenzoesäureester 1 und Thiobenzoesäure-O-methylester (7) liefern bei der Elektroreduktion in Gegenwart von Alkylhalogeniden die Benzaldehyd-dithioacetale 2 bzw. -monothioacetale 8; in Gegenwart von Acetanhydrid entsteht aus dem Ethylester 1b das S-Acylal 3b.  -  Die Koelektroreduktion von Dithiopropionsäure-methylester (4) mit Alkylhalogeniden ergibt neben den Dithioacetalen 5 die Keten-dithioacetale 6.  -  Aus voltammetrischen Messungen werden Rückschlüsse auf den Reaktionsmechanismus gezogen.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019800316
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  • 10
    Electronic Resource
    Electronic Resource
    Darstellung neuer vicinaler Tricarbonylverbindungen und einiger ihrer Schwefelanaloga (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1694-1711 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation of New Vicinal Tricarbonyl Compounds and Some of Their Sulfur AnaloguesMesoxalamides 5, benzoylglyoxylamides 19, and pivaloylglyoxylamides 26 are prepared from the corresponding malonamides 4, benzoylacetamides 17 and pivaloylacetamides 24, respectively, by suitable oxidation reactions. Some of the sulfur analogues of 5, 19, and 26, including the first stable 2-thiomesoxalic acid derivative 11b, are also obtained. The spectroscopic properties of the compounds are discussed.
    Notes: Durch geeignete Oxidationsreaktionen gelingt die Überführung der Malonamide 4 in Mesoxalamide 5, der Benzoylacetamide 17 in Benzoylglyoxylamide 19 und der Pivaloylacetamide 24 in Pivaloylglyoxylamide 26. Auch Schwefelanaloga von 5, 19 und 26, darunter das erste stabile 2-Thiomesoxalsäurederivat 11b sind zugänglich. Die spektroskopischen Eigenschaften der dargestellten Verbindungen werden diskutiert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319831006
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