Rhodium (Chief Bee)
12-06-01 18:13
No 244976
      P2P from Mn(III)/Benzene/Acetone (Part II)  Bookmark   

I have now finished a draft of the document on the Mn(III)-Catalyzed Condensation of Benzene and Acetone: ../rhodium/chemistry /p2p.manganese.html
The preparation of Manganese(III)Acetate is already on my page too: ../rhodium/chemistry /manganous.acetate.html

As we can see in the document I made on my page, both P2P and 2,5-MeO-P2P can be made in approximately 40% yield (based on Mn3+) already with the procedure not optimized for efficiency, and that the unreacted starting materials can be reused for another run, thereby increasing the yield drastically, perhaps approaching quantitative.

What can be seen also is that because the acetonyl radical does not add selective at all to the benzene ring (a mixture of ortho, para and meta isomers are produced, with the ortho isomer in the highest yield) the reaction is only useful with unsubstituted and 1,4-substituted benzene derivatives.
 
Now, when the necessary outline has been compiled for the reaction, are there any takers on the practical test of the method?

Now, I have a few questions to ask the crowd:

I know that the original reference for the reaction appeared in CA 77, 151620 (1972). Is it correct to assume that that reference corresponds to the original publication Bulletin of the Academy of Science of the USSR 21(7) 1626 (1972)? In that case I already have the full text of that one-page article (written by Vinogradov, Verenchikov & Nikishin) - I don't know what publication it comes from, I just know that the text corresponds to what's written in CA 77, 151620 (1972). If the CA reference does NOT equal the USSR article above, I'd like to know what publication the CA ref points to, as well as obtaining the USSR ref above.

I would also like to get my hands on the text of the following publications, all pertaining to the reaction we are interested in here, please post if you can:

Journal of Organic Chemistry of the USSR 12, 2245 (1975)
Min, Aksenov, Vinogradov & Nikishin, Izv. Acad. Nauk SSSR, Ser. Chim., 2292 (1979); CA 92, 110239s (1980)
 
 
 
 
    bottleneck
(Stranger)
12-06-01 23:43
No 245084
      Re: P2P from Mn(III)/Benzene/Acetone (Part II)  Bookmark   

Wow.