Turkish Journal of Chemistry
DOI
10.3906/kim-1711-49
Abstract
A rapid and selective iron-mediated reductive Claisen rearrangement of various prop-2'-enyloxyanthraquinones and 2'-chloroprop-2'-enyloxyanthraquinones to 1-hydroxy-2-(prop-2'-enyl)anthraquinones and anthrafurandiones is presented. All reactions are carried out in a mixture of ionic liquids, [Bzmim]Cl (1-benzyl-3-methylimidazolium chloride) and [Hmim]BF$_{4}$ (1-methylimidazolium tetrafluoroborate), in short reaction times (5-35 min). Our study showed that 1-(prop-2'-enyloxy)anthraquinone is more active than 1-(2'-chloroprop-2'-enyloxy)anthraquinone to perform this rearrangement.
Keywords
2'-Chloroprop-2'-enyloxyanthraquinone, anthrafurandione, Claisen rearrangement, iron, ionic liquid
First Page
883
Last Page
895
Recommended Citation
NADALI, SAMANEH; KHOSHROO, ALI; and AGHAPOUR, GHASEM
(2018)
"Efficient reductive Claisen rearrangement of prop-2'-enyloxyanthraquinones and 2'-chloroprop-2'-enyloxyanthraquinones with iron powder in ionic liquids,"
Turkish Journal of Chemistry: Vol. 42:
No.
3, Article 22.
https://doi.org/10.3906/kim-1711-49
Available at:
https://journals.tubitak.gov.tr/chem/vol42/iss3/22
