Douchermann
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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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| 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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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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Would you believe "eugenol.wacker.anomaly".pdf
http://psychedelichosting.info/Ionium/Rhodium/pdf/
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Douchermann
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Thats perfect S.C. Wack, thank you very much. Perfect... but frustrating.
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