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Synthesis 1997; 1997(4): 423-424
DOI: 10.1055/s-1997-1202
short paper
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Direct Lithiation of Methyl Isothiocyanate: A New Convenient Synthesis of Mono-, Bis- and Tris(trimethylsilyl)methyl Isothiocyanate

Lambert Brandsma1 , Nina A. Nedolya2 , Hermann D. Verkruijsse3 , Boris A. Trofimov4
  • 1Department of Preparative Organic Chemistry, Debye Institute, University of Utrecht, Padualaan 8, NL-3584 CH, Utrecht, The Netherlands, E-mail: L.brandsma@chem.ruu.nl
  • 2Irkutsk Institute of Organic Chemistry, Russian Academy of Sciences, Siberian Branch, Faborsky Street 1, RUS-664033 Irkutsk, Russia
  • 3Department of Preparative Organic Chemistry, Debye Institute, University of Utrecht, Padualaan 8, NL-3584 CH, Utrecht, The Netherlands
  • 4Irkutsk Institute of Organic Chemistry, Russian Academy of Sciences, Siberian Branch, Faborsky Street 1, RUS-664033 Irkutsk, Russia, E-mail: bat@acet.irkutsk.su
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Publication History

Publication Date:
31 December 2000 (online)

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Methyl Isothiocyanate/chlorotrimethylsilane mixtures in THF are readily converted with lithium diisopropylamide at -95°C to give trimethylsilylmethyl isothiocyanate, bis(trimethylsilyl)methyl isothiocyanate, and tris(trimethylsilyl)methyl isothiocyanate in 50-95% yields.

methyl isothiocyanate -metallation of - methyl isothiocyanate -trimethylsilylation of