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Synthesis 1994; 1994(1): 107-110
DOI: 10.1055/s-1994-25415
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Novel N-(Alkylthiomethyl)iminophosphoranes and Their Application to the Syntheses of New Functionalized N,S-Acetals

Alan R. Katritzky* , Jinlong Jiang, John V. Greenhill
  • *Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-2046, USA
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Publication Date:
17 September 2002 (online)

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Reaction of thiolates with (1-triphenylphosphorylideneaminomethyl)benzotriazole (betmip, 1) gave novel N-(alkylthiomethyl)-iminophosphoranes 3 which were transformed, without isolation and in high yields, to N-(alkylthiomethyl)benzalimines 4, N-(alkyl)-N′-(alkylthiomethyl)carbodiimides 5 and N-(alkylthiomethyl)-amides 7 by treatment with araldehydes, tert-butyl isocyanate or acyl chlorides, respectively. N-(Alkylthiomethyl)- N′-tert-butylcarbodiimides 5 provide N-(alkyl)-N′-(alkylthiomethyl) ureas 6 in good yield.