Author Topic: JACS,106,24,(1984) 7573-7578; ammonium persulfate CuII complex as an oxidizer  (Read 915 times)

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dormouse

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Author  Topic:   JACS,106,24,(1984) 7573-7578; ammonium persulfate CuII complex as an oxidizer 
drone 342
Member   posted 10-13-98 07:42 PM          
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This really is something; using phenylpropenes as the starting material, persulfates form an intersting complex with CuII+ compounds which oxidize the aforementioned starting material into phenyl acetones and benzaldehydes. If you check your chem catalogs, you'll see ammoniumpersulfate is very inexpensive, and if you check the the reaction conditions, you'll see they're very agreeable (AcOH:H2O, 100 deg C.)
Heck, they even manage to find a way to convert styrene itself into phenylacetone


Rhodium
Administrator   posted 10-14-98 07:41 PM          
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Hey, where did you find the third aliphatic carbon when making P2P from styrene?
What they DID accomplish was the conversion of alpha-methylstyrene to P2P and phenylpropanal (which can be isomerized to P2P with H2SO4 or HgCl2), as well as oxidizing propenylbenzene to P2P.


drone 342
Member   posted 10-14-98 09:15 PM          
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Right you are. There are ways of making phenylacetone from styrene, but the article mention uses methylstyrene. My appologies for the confusion. Still, this is a nice article, using cheap reagents to do something we're all interested in, and it does it reasonably well.
-drone #342


Rhodium
Administrator   posted 10-14-98 09:42 PM          
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Yup.
The useful reactions are the following, where the 'conversion' figures denotes how many percent of the substrate that reacted, and the 'purity' how much of the product that was the desired:

* alpha-Methylstyrene in HOAc to give 2-phenylpropanal (97% conversion, 91% purity)
* Propenylbenzene in HOAc to give P2P (55% conversion, purity 82%)
* Propenylbenzene in Acetonitrile to give P2P (55% conversion, purity 88%


 
drone 342
Member   posted 10-15-98 09:05 AM          
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Say, how is 2-phenylpropanal important? I think you may have mentioned something about isomerizing this, but *how*?
-drone #342


Osmium
Member   posted 10-15-98 12:13 PM          
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2-phenylpropanal can be isomerised to P2P by action of cold H2SO4 or HgCl2. Comes from an old german ref. It's on Rhodium's site.
 
drone 342
Member   posted 10-15-98 12:31 PM          
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What I meant was, what's the mechanism? I can't see why this should isomerize like that. I'm not saying it doesn't, but HOW?
-drone #342