The reaction of carbonyldiimidazole with alcohols to form carbamates and N-alkylimidazoles

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Abstract

The reactions of non-benzylic primary and secondary aliphatic alcohols with carbonyldiimidazole (CDI) afford the corresponding carbamates but not N-alkylimidazoles. For benzylic primary alcohols, formation of N-alkylimidazoles proceeds reasonably at 170 °C in several different solvents and occurs by way of the initially formed carbamate. However, under these rather forcing conditions, or even at lower reaction temperatures, elimination is a significant side reaction for benzylic secondary alcohols with β-hydrogen atoms. With one exception, reactions of six N,N-disubstituted β-aminoalcohols with CDI to form N-alkylimidazoles proceed under relatively mild conditions and may occur by way of an aziridinium intermediate.

Original languageEnglish (US)
Pages (from-to)2540-2544
Number of pages5
JournalSynthesis
Issue number15
DOIs
Publication statusPublished - Oct 18 2004

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Keywords

  • Alcohols
  • Alkylations
  • Carbamates
  • Carbonyldiimidazole (CDI)
  • N-alkylimidazoles

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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