It's getting confusing in this thread, if I get it right, then noj's tests were not giving amine, V_Lights says he got some amine (or not, not really clear with those ultrashort reportings of him and the others, Flip etc), and I see only one method mentioned, which seem to give a consistent yield, Chromics on Rhodiums pages.
The thermal rearrangement tests (just heat the DISTILLED epoxide at 1 atm to 283-284C, keep it there 20 minutes, then it's ketone, or better, use vacuum at 9 Torr up to 140-145C and reflux with an aircondenser inbetween for approx. 2 hours to get the same ketone, then distill under vacuum to get pure ketone) seems questionable till now, still no real aminations?
Please give me any postnrs if there is one I oversee! I'm getting desperate from the overload of posts lately on the subject of thermal and catalytic (15% H2SO4) rearrangements, and they hop from one thread to another, why not start a new thread with all real factual testreports, and no blahblabla please from people who want attention.
Here's some reading stuff from the Search Engine :
Post 227831
(uemura: "Ketones from Propenylbenzenes via the di-bromides", Novel Discourse) 62 posts, Ketones from Propenylbenzenes via the di-bromides, Uemura's Höring refs etc. Novel forum. After Rhodiums
Post 232994
(Rhodium: "Re: Ketones from Propenylbenzenes via the di-bromides", Novel Discourse) it gets again really interesting. ""I don't understand why noone has tested the hypochlorite or hypobromite route to the halohydrin, and then made the epoxide from that with a base. It is OTC, and very simple." I also don't understand, that's layed out in Uemura's starting post up there in this thread.
Post 218193 (missing)
(Ritter: "LiI catalyzed pinacol rearrangement possible?", Chemistry Discourse) Li catalysed pinacol rearrangement possible? Chemistry forum.
Post 235999
(Chromic: "Asarone epoxidation by Oxone", Chemistry Discourse) Chromic's
Asarone epoxidation by Oxone.
Post 241293
(uemura: "Properties of some epoxides", Novel Discourse) Properties of some epoxides, Epoxide Synthesis (described for
anethole) and
Asarone Epoxide Rearrangement both exellent write ups, wished everybody confirm to this kind of perfectionism and clarity!!!
And Rhodium's
Asarone glycol distillation.
TLC techniques by Uemura and Osmium. Plus UV lamp recognision of spots on TLC plates.
Post 241585
(uemura: "Boiling Point Measurement", Chemistry Discourse) Uemura's Boiling Point Measurement,
epoxide thermal rearrangment.
Post 265056
(Osmium: "Re: Thermal isosafrole epoxide rearrangement trial", Methods Discourse) Osmium's way of isomerization of an epoxide to the ketone under vacuum.
Post 264485
(Vibrating_Lights: "Thermal isosafrole epoxide rearrangement trials", Methods Discourse) Same thread, Thermal isosafrole epoxide rearrangement trials of Vibrating_Lights (=Flip?):
""Yes only from the atm distillation of the un distilled epoxide the ketone from the crude rearrangement did not aminate. however the ketone that was produced with the previously vac distilled epoxide did aminate in 66% yeild. (V_L)""
Noj however reports a failure to aminate: ""Ok, swim has some fluid in the freezer that won't freeze. The H2SO4 hydrolysis was done, then tried a bisulfite adduct, which failed. Tried to aminate anyway, and it failed.""
V_L tried a microwave: ""20 mins on high did nothing to epoxide. Not saying it wont work but need to rig the microwave better before any thing else is attempted."" Failed till today.
So, conclusion: who got a thermal rearrangement really working, and what yield of amine they got?
Only report is from V_L, 66%. No one else on Isosafrole. A bit meager result to bet your money on.
LT/
PS: And the latest thread
Post 243262
(uemura: "Epoxide Rearrangement Example", Methods Discourse) Epoxide Rearrangement Example.
PSII:
Post 280823
(cheeseboy: "Re: mdp2p from oxone", Methods Discourse) mdp2p from oxone thread, Cheeseboy claims success, but has not aminated yet, keeps us sitting on the tip of the chair untill he does!
WISDOMwillWIN