try this
Re: Sesamol part 2 ver. Bucherer rearrangement, Meerwein arylation
« Reply #20 on: October 29, 2011, 01:29:17 PM »
1.pdf
(130.57 kB - downloaded 20 times.)
Topic: Sesamol part 2 ver. Bucherer rearrangement, Meerwein arylation (Read 308 times)
POSEIDON
- Subordinate Wasp
- Posts: 116
1.pdf
(130.57 kB - downloaded 20 times.)akcom
- Dominant Queen
- Posts: 430
Re: Sesamol part 2 ver. Bucherer rearrangement, Meerwein arylation
« Reply #21 on: October 30, 2011, 03:11:52 PM »
sigmatropic rearrangements like the one you referenced typically lead to ortho substitutions due to the nature the of the transition state. Not sure that it would be useful in this context.
atara
- Dominant Queen
- Posts: 256
Re: Sesamol part 2 ver. Bucherer rearrangement, Meerwein arylation
« Reply #22 on: October 30, 2011, 07:27:49 PM »
That rearrangement on sesamol has been used to synthesize carpacin, a rather obvious precursor for MMDA-2. The problem is that it requires allyl bromide and dimethyl sulfate, or equivalent reagents. It's just an aromatic Claisen rearrangement, and IIRC Shulgin himself said that it usually selects the 6-position (the "correct" one) over the 2-position on sesamol.
I think it's off-topic, though, since it leads to an entirely different drug. If you do a Claisen on sesamol, you don't get safrole because the OH is still there.
I think it's off-topic, though, since it leads to an entirely different drug. If you do a Claisen on sesamol, you don't get safrole because the OH is still there.