UndergroundChemist
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Capsaicin Wacker Oxidation?
Would a wacker oxidation of Capsaicin result in
Would it even work for that matter?
I'm thinking CuCl as Oxidation catalyst and Palladium Chloride II
dissolved in a solution of DMF and H2O? :?
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Nicodem
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Thread Moved
10-4-2014 at 09:37 |
zed
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Ummm. Might be concerned about the 5-position on that aromatic ring. That phenolic -OH...activates the ring in many cases. Can the Wacker be
performed on Eugenol? That might be a good test question. If you can't successfully oxidize Eugenol or its isomer, forget it. Also, the Wacker is
usually utilized to synthesis methyl ketones. I don't see any in your structure.
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Chemosynthesis
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Agreed. I don't see any phenols in this article:
Org. Lett., 2012, 14 (13), pp 3237–3239
DOI: 10.1021/ol301240g
and this indicates no:
Tetrahedron Letters, Vo1.30, No.6, pp 759-762, 1989
DOI: 10.1016/S0040-4039(01)80302-6
OP: Doubt you have any 2-(tert-butyldiphenylsilyl)ethyl (TBDPSE) protecting agent lying around to try out given your psilocin question. With your
name and subject matter, it's pretty indicative that you're trying to apply the chemistry without learning it first. If you want some advice from
someone in legitimate pharmacology, you're not setting yourself up for success. Walk before you run. There's nothing wrong in seeing a reaction and
wondering how it works, but I get the very distinct impression you're seeing a reaction and wondering if you can profit from it.
[Edited on 12-4-2014 by Chemosynthesis]
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UndergroundChemist
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Quote: Originally posted by zed  | | Ummm. Might be concerned about the 5-position on that aromatic ring. That phenolic -OH...activates the ring in many cases. Can the Wacker be
performed on Eugenol? That might be a good test question. If you can't successfully oxidize Eugenol or its isomer, forget it. Also, the Wacker is
usually utilized to synthesis methyl ketones. I don't see any in your structure. |
According to this it doesn't matter where if it's a phenol or eugenol or anything it just needs a chain connected to a carbon with a double bond to a another
carbon. What I'm worried about is that it wont work because the double bond is then connected to another chain.
"Im a noob so I might just be wrong"
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Chemosynthesis
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Where do you see that? That's not what I take away from that at all, and my citations should demonstrate it.
I believe that just gives two constitutional isomers.
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