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

Research output: Contribution to journalArticle

20 Citations (Scopus)

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
StatePublished - Oct 18 2004

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Carbamates
Alcohols
Hydrogen
Atoms
Temperature

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

The reaction of carbonyldiimidazole with alcohols to form carbamates and N-alkylimidazoles. / Tang, Yuanqing; Dong, Yuxiang; Vennerstrom, Jonathan L.

In: Synthesis, No. 15, 18.10.2004, p. 2540-2544.

Research output: Contribution to journalArticle

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