Sciencemadness Discussion Board

Capsaicin Wacker Oxidation?

UndergroundChemist - 10-4-2014 at 08:37

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? :?

zed - 11-4-2014 at 16:23

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.

Chemosynthesis - 11-4-2014 at 19:58

Quote: Originally posted by zed  
Ummm. Might be concerned about the 5-position on that aromatic ring.

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]

UndergroundChemist - 19-4-2014 at 08:39

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"

Chemosynthesis - 19-4-2014 at 13:49

Quote: Originally posted by UndergroundChemist  

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.

Where do you see that? That's not what I take away from that at all, and my citations should demonstrate it.
Quote: Originally posted by UndergroundChemist  
What I'm worried about is that it wont work because the double bond is then connected to another chain.

I believe that just gives two constitutional isomers.