Ultra-high pressure direct syntheses of bis(imidazolium-3-yl)alkane dichlorides

Laurence M. Harwood, Phillip Pitt, Janet L. Scott, Dora Sousa

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

The ultra-high pressure Menshutkin reaction of N-substituted imidazoles and α,ω-dichloroalkanes provides access to a wide variety of bis(imidazoliumyl)alkane dichlorides in an efficient, one-pot process. Although the substitution reactions of dichloromethane at ambient pressure can be exceedingly slow, at 1.9 GPa, syntheses are usually quantitative in under 24 h. Reactions involving congested imidazole starting materials, that otherwise terminate after formation of the mono-imidazolium salt, are driven to the bis-imidazolium salt at 1.9 GPa. The rates of reaction increase with α,ω-dichloroalkane chain length, decrease with increasing bulk and imidazole N-substituent length, and the reactions of the more hindered imidazoles are more sensitive to the pressure-rate enhancement.

Original languageEnglish
Article number130639
Pages (from-to)1-8
Number of pages8
JournalTetrahedron
Volume75
Issue number44
Early online date26 Sep 2019
DOIs
Publication statusPublished - 1 Nov 2019

Keywords

  • Hyperbaric
  • Imidazolium salts
  • Ionic liquids
  • Menshutkin reaction
  • Ultra-high pressure

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Ultra-high pressure direct syntheses of bis(imidazolium-3-yl)alkane dichlorides'. Together they form a unique fingerprint.

Cite this