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  • 1
    Electronic Resource
    Electronic Resource
    ESR-Untersuchungen an Carbonsäureestern, 12. Bildung von 9-Fluorenon-Radikalanionen durch Elektrolyse von sterisch gehinderten Biphenyl-2-dithiocarbonsäure-methylestern (1989)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 122 (1989), S. 1009-1012 
    Details
    ISSN: 0009-2940
    Keywords: ESR, biphenyl-2-carbodithioates ; 9-Fluorenones, sterical hindrance ; Radical anions ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Formation of 9-Fluorenone Radical Anions during Electroreduction of Sterically Hindered Methyl Biphenyl-2-dithiocarboxylatesESR signals due to the radical anions of the 9-fluorenones 4 and 5 are observed besides the spectra of the radical anions of the tert-butylated methyl biphenyl-2-dithiocarboxylates 1 and 2 if the latter are electroreduced in dimethylformamide or acetonitrile. A mechanism for the observed reaction is suggested.
    Notes: Nach Elektroreduktion der tert-butylierten Biphenyl-2-dithiocarbonsäure-methylester 1 und 2 in Dimethylformamid oder Acetonitril beobachteten wir neben den ESR-Spektren der entsprechenden Radikalanionen die Signale von Radikalanionen der 9-Fluorenone 4 und 5. Ein Mechanismus für die Bildung der 9-Fluorenon-Ketyle wird vorgeschlagen.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19891220534
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    C,C-Verknüpfungen mit Schwefel-stabilisierten Carbanionen, 2[1] Reaktionen des 2-(Methylthio)thiolan-Carbanions mit Elektrophilen[2] (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 1641-1646 
    Details
    ISSN: 0009-2940
    Keywords: Thioacetals, semicyclic ; Carbanions ; Alkylation ; Hydroxyalkylation ; Diastereoselectivity ; Thiolanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: C,C Coupling with Sulfur-Stabilized Carbanions, 2[1]. - Reactions of the 2-(Methylthio)thiolane Carbanion with Electrophiles[2]The „semicyclic” thioacetal 2-(methylthio)thiolane (4) is easily prepared from thiolane (tetrahydrothiophene). It is readily deprotonated by butyllithium to give the lithium derivative 5, which reacts with alkyl halides, saturated and α,β-unsaturated carbonyl compounds, and benzonitrile to form the alkyl derivatives 6, carbinols 7, allyl alcohols 8, and - after hydrolysis - the ketone 9. The diastereoselectivity of the C,C coupling reaction is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250720
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  • 3
    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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    Paper (German National Licenses)
  • 4
    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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    Paper (German National Licenses)
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