Author Topic: iodosafrole writeup  (Read 650 times)

no1uno

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Re: iodosafrole writeup
« Reply #20 on: November 21, 2009, 06:23:28 PM »
Here are some, in this they view the monofuran as a mescaline-analogue, in this the inestimable Dr Nicholl's shows up in earnest and finally, in THIS paper we see the use of 1-Br-2-Cl-ethane directly on phenols to form the furan ring(s)... Which is ironic indeed, given that Shulgin, Nicholl's, et al, had previously done so using Grignard (rather than BuLi) conditions to affect ring-closure (HERE)
« Last Edit: November 21, 2009, 06:44:12 PM by no1uno »
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zzhuchila_clocker

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Re: iodosafrole writeup
« Reply #21 on: November 21, 2009, 07:38:55 PM »
no1uno, that is very interesting, concerning dihydrofuranyl rormation with bromochloroethane.  but the links are not opening, probably erowid is down. what reaction is it, is it a o-alkylation of phenols followed by coupling with some lewis acid, or c-alkylation of phenolate ion followed by o-alkylation? or what reagents do they use? (just because i can not view the paper)
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no1uno

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Re: iodosafrole writeup
« Reply #22 on: November 22, 2009, 01:19:49 AM »
They are opening still for me...

This isn't new stuff - #80 F-22 & #79 F-2 are both in PIHKAL (PIHKAL naming)... While they were failures as it turns out, that doesn't mean that the subsequent SAR's (per Nicholl's et al) are flawed, it might simply be that by leaving that 3-MeO in place then forming the 4,5-furanyl on the p-hydroxy, then a rigid, 3-carbon amine could be formed rather simply which might well be of interest (intriguingly - where would MDMA, etc. fit in the putative SAR concept of Nicholl's et al?)
« Last Edit: November 22, 2009, 01:32:23 AM by no1uno »
"...     "A little learning is a dang'rous thing;
    Drink deep, or taste not the Pierian spring:
    There shallow draughts intoxicate the brain,
    And drinking largely sobers us again.
..."