Edit: Aagh, you beat me to it Nicodem! How did you have these extra papers too?!
At least I have them in PDF. Oh well, someone feel free to delete my post
/EditGreat find lutesium!
For a while I had been wondering whether this reaction would be possible. I would like to try something similar on propiophenone, with permanganate and a halide salt in glacial acetic acid. My idea was based on the
Novel Bromination Method for Anilines and Anisoles Using Ammonium Bromide and H2O2 in Acetic Acid
(
https://www.thevespiary.org/rhodium/Rhodium/chemistry/aromatic.bromination.nh4br-h2o2.html).
Here is the article in PDF, as well as two other related articles by the same authors (halogenation of arenes with the same permanganate-HX system) which I found a few weeks ago:
A Convenient Halogenation Procedure for the Preparation of alpha-Halocarbonyl CompoundsSheng-Fan Cheng, Ching-Shan Lin and Lilian Kao Liu*
Journal of the Chinese Chemical Society, 1997,
44, 309-312
AbstractExcept for substituted acetophenones (
p-Y-C
6H
4COCH
3, Y=H, Br, CH
3O), simple ketones,
beta-ketoesters and 1,3-diketones reacted smoothly with a preformed homogeneous mixture of hydrochloric acid and potassium permanganate in acetonitrile to give moderate to good yields of the corresponding
alpha-chlorocarbonyl compounds. Mixtures of
alpha-chloro- and
alpha,
alpha-dichlorocarbonyl compounds were obtained for substituted acetophenones. Brominations proceeded similarly with higher yields when the hydrochloric acid was replaced with hydrobromic acid.
Reaction of Aromatic and Unsaturated Compounds with the Potassium Permanganate/HCl (HBr) Acetonitrile ReagentLilian Kao Liu* and Ching-Shan Lin
Journal of the Chinese Chemical Society, 1996,
43, 61-66
AbstractAddition of hydrochloric or hydrobromic acid to a solution of potassium permanganate in acetonitrile produced a homogeneous mixture, which is suitable for laboratory chlorination or bromination, respectively. Aromatic compounds more reactive than alkylbenzenes can be chlorinated or brominated without additional catalyst. Alkenes and alkynes give the corresponding vicinal dihaloalkanes and vinyl halides. All reactions complete within two hours under mild condition (25-60°C) with excellent to moderate yields.
Iodination with Potassium Permanganate/Hydroiodic Acid/Acetonitrile ReagentJyh-AnChen, Ching-Shan Lin and Lilian Kao Liu*
Journal of the Chinese Chemical Society, 1996,
43, 95-99
AbstractIodination of various aromatic amines proceeds smoothly with a preformed homogeneous mixture of hydroiodic acid potassium pennanganate in acetonitrile.
para-Substituted products were obtained in high yields (71-78%) within twelve hours at room temperature.
With a slight modification of the permanganate, hydroiodic acid and substrate ratio, iodination of alkynes to
vic-diiodoalkenes can be carried out at 60
oC in 65-87% yield.