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Author: Subject: Palladium (II) catalyzed oxidation of Eugenol
Douchermann
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[*] posted on 14-7-2008 at 00:55
Palladium (II) catalyzed oxidation of Eugenol


I searched thoroughly and could not find any information on a definite procedure. I figured it would be analogous to the safrole oxidation, but after reading through some of the hive archives, I came across some very limited information explaining that the wacker oxidation does not produce the corresponding carbonyl from eugenol, as it does other propenyl compounds. Key phrases such as "isn't fully compatible" make me think that slight modifications would render a procedure that is successful. Does anyone have any information on this whatsoever?
The article is

Anomalous Behaviour of Substituted Allyl Benzenes in Palladium(II) Catalysed Reaction
Meera Iyer, Dinesh N. Rele and G.K. Trivedi

If anyone could point me to this article that would be great, as I couldn't find it through multiple searches.




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Nicodem
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[*] posted on 14-7-2008 at 01:57


Quote:
Originally posted by Douchermann
Anomalous Behaviour of Substituted Allyl Benzenes in Palladium(II) Catalysed Reaction
Meera Iyer, Dinesh N. Rele and G.K. Trivedi

If anyone could point me to this article that would be great, as I couldn't find it through multiple searches.

The reference is apparently:
Anomalous behavior of substituted allylbenzenes in palladium(II) catalyzed reaction.
Iyer, Meera; Rele, Dinesh N.; Trivedi, G. K.
Tetrahedron Letters, 30 (1989) 759-762.




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Panache
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[*] posted on 14-7-2008 at 02:41


From a purely speculative basis, i would imagine safrole and eugenol to behave markedly differently if subjected to the same wacker oxidation conditions. Thus if the paper stated refers to these differences as anomalies i think this is ridiculous.

It would be tempting to view these two compounds as practically identical, given baring one bond they are, it is rather an important difference however.
With safrole you have really little to concern yourself with should you attempt transforms on the double bond on the side chain as the heterocyclic ether subsitutient is fairly impervious to conditions that would readily epoxidise, hydrogenate or halogenate. If i recall the wacker oxidation it is rather an elegant piece of chemistry where Pd(II) complexes an olefin, transition state conditions prevail allowing for some oxidative intermediate to add. Providing you can get all three species into solution and ensure no side reactions (as the Pd is catalytic, any small affect on it has a large effect on the rxn sucess). It works nicely for some fatty acid amides i recall but i may be incorrect here.
There is no way the phenolic OH on eugenol will not preferentially bind/complex to the precious and sensitive Pd(ii). I imagine the di-Methoxy ether would behave analogously to safrole.

As stated earlier these are just thoughts. I would be curious to know how someone better versed in organic chemistry would view the situation as it appears on paper, as when i re-read my post it seems to be rather a wank and i would appreciate knowing how better an argument, for what i'm trying to speculate at, could be stated.




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S.C. Wack
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[*] posted on 14-7-2008 at 02:47


Would you believe "eugenol.wacker.anomaly".pdf
http://psychedelichosting.info/Ionium/Rhodium/pdf/
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Douchermann
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[*] posted on 14-7-2008 at 09:57


Thats perfect S.C. Wack, thank you very much. Perfect... but frustrating.



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