Synthesis 1990; 1990(6): 477-480
DOI: 10.1055/s-1990-26910
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Selective Monocarbamoylation of Symmetrical Diols with Alkyl Halides and Potassium Cyanate Using Phase-Transfer Catalysis

Mahavir Prashad* , John C. Tomesch, William J. Houlihan
  • *Sandoz Research Institute, East Hanover, NJ 07936, USA
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Publication History

Publication Date:
17 September 2002 (online)

A convenient method for the selective monocarbamoylation of diols by reaction with alkyl isocyanates, generated in situ from alkyl halides and potassium cyanate under phase-transfer catalysis, is described. Under these conditions the ease of reaction shows the following order cis-diols > trans-diols and diols > monoalcohols. An increase in the number of methylene groups between two hydroxyl groups lead to a decrease in product yields. A plausible mechanism to explain these results is proposed.