Jump to main content
Jump to site search

Issue 4, 2011
Previous Article Next Article

Rapid and efficient protic ionic liquid-mediated pinacol rearrangements under microwave irradiation

Author affiliations

Abstract

Several protic ionic liquids were tested as potential mediators for pinacol rearrangements employing microwave irradiation. Using hydrobenzoin as a model substrate, the optimal conditions were found to be heating at 80 °C for 5 min using H2SO4:triethylamine as the ionic liquid. A key feature of this reaction was to keep the microwave power low (20 W) to avoid ionic liquid degradation. Application of these conditions to triphenylethylene glycol gave rearrangement products in high yield and purity, while phenylethylene glycol and styrene oxide gave pinacol products that underwent a cascade aldol condensation. These conditions represent an efficient means by which pinacol rearrangements can be carried out while avoiding the use of strong Brønsted acids, high temperatures and extended reaction times.

Graphical abstract: Rapid and efficient protic ionic liquid-mediated pinacol rearrangements under microwave irradiation

Back to tab navigation

Supplementary files

Publication details

The article was received on 13 Dec 2010, accepted on 19 Jan 2011 and first published on 21 Feb 2011


Article type: Communication
DOI: 10.1039/C0GC00916D
Green Chem., 2011,13, 813-816

  •   Request permissions

    Rapid and efficient protic ionic liquid-mediated pinacol rearrangements under microwave irradiation

    L. C. Henderson and N. Byrne, Green Chem., 2011, 13, 813
    DOI: 10.1039/C0GC00916D

Search articles by author

Spotlight

Advertisements