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  • 1
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: α-Halo-substituted Amines, XXXVII. α-Chloro-β-dialkylaminoethane-sulfonamides, -sulfones and -sulfoxidesα-Chloroalkyllithio- and α-chloroalkyldilithio-sulfones and -sulfonamides (2, 5) react with one or two equivalents of α-haloamines to the corresponding α-chloro-β-dialkylamino or α-chloro-β.β'-bisdialkylamino derivatives (3, 6). NMR-spectra of 3 and 6 show second order splitting patterns indicating the presence of diastereotopic methylene protons, which is similar in the case of the analogous α-chloroalkylsulfonamides 11 and 13. Treatment of lithio-α-chloromethyl-phenyl sulfoxide (15) with α-haloamines affords the β-dialkylamino derivatives 16.
    Notes: α-Chlor-alkyllithium- und α-Chlor-alkyldilithium-sulfone und -sulfonamide (2, 5) reagieren mit 1 bzw. 2 Moll. α-halogeniertem Amin zu den entsprechenden α-Chlor-β-dialkylamino-3 bzw. α-Chlor-β.β'-bis-dialkylamino-Derivaten 6. Die NMR-Spektren von 3 und 6 weisen Aufspaltungen höherer Ordnungen auf, die für das Vorliegen diastereotoper Methylen-Protonen sprechen; ähnlich liegen die Verhältnisse bei den analogen α-Chlor-alkylsulfonamiden 11 und 13. Aus Lithium-α-chlormethyl-phenyl-sulfoxid (15) und α-Halogen-methylaminen entstehen [α-Chlor-β-dialkylamino-äthyl]-phenyl-sulfoxide (16).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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