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Synthesis 1991; 1991(8): 637-640
DOI: 10.1055/s-1991-26532
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Lithium-N-lithiomethyldithiocarbamate: Neue N-Alkylaminomethylanion-Äquivalente II1 Untersuchungen zur Anwendungsbreite der Methode: Sterisch gehinderte und aromatische N-Methylamine

Hubertus Ahlbrecht* , Christine Schmitt, Dieter Kornetzky
  • *Fachbereich Chemie der Universität Gießen, Institut für organische Chemie der Justus-Liebig-Universität, Heinrich-Buff-Ring 58, D-6300 Gießen, Germany
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Publication Date:
29 April 2002 (online)

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Lithium N-Lithiomethyldithiocarbamates: New N-Alkylaminomethyl Anion Equivalents II1 Investigations on the Scope of the Method: Sterically Hindered and Aromatic N-Methylamines The scope of the methyl deprotonation of secondary methylamines protected as lithiodithiocarbamates has been investigated. Deprotonation is possible with branched N-alkylmethylamines such as the cyclohexyl derivative but failed in the case of N-tert-butylmethylamine. With aromatic methylamines such as N-methylaniline regioselective methyl- as well as ortho-deprotonation is possible depending on the base used.