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UW-Madison CHEM 345 - Preparation of Phenols by Phthaloyl Peroxide Mediated Oxidation of Arenes

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Preparation of phenols by phthaloyl peroxide mediated oxidation of arenesExtra Credit Paper Review 1Victoria Chen Professor Schomaker This article outlines the protocol to installing hydroxls onto arenes through the direct replacement of C-H bonds with C-O bonds. This direct oxidation avoids the need to pre-functionalized the substrate, use precious metals, introduce directing groups or use a strong bronsted or lewis acid. In this procedure, it uses the synthesis of phthaloyl peroxide for the creation of a mesitylene. From this article, I learned about arenes and the synthesis of arenes. Arenes are aromatic rings with a methyl group attached. Typically to synthesize an arene, one needs to use strong acids in combination with oxidants to create a harsh environment for the reactions can occur; however, with the procedure found within the article this is no longer the case. Instead of these harsh conditions and high temperatures to accelerate the reaction, a more simple procedure can be followed. This involves >80°C and a phthaloyl peroxide solution. In class, we discussed many other ways to install hydroxls onto an arene. These include a SnAR reactions, Grinard Reagents, and placing directing groups on the aromatic ring first. In an SnAR reaction one can use NaOH as the solvent to attach a hydroxyl group onto a ring with a directing group already on it. A Grignard reaction involves attaching a MgBr group and then using and excess of O2 in an acidic solution to attach the hydroxyl group. Many of the reactions that we learned in class need to introduce directing groups or use strong Bronsted or Lewis acids.This was the main problem this article highlights when trying to attach a hydroxyl group to an arene. Because of these problems, they created a solution that could avoid these harsh conditions.There were two main things that I found interesting when reading this article. The first was that I found it amusing that there were so many ways in which you could handle the solutionwrong to cause it to explode. This was due to the friction sensitivity from the byproduct of phthaloyl peroxide. Due to this, much of the procedure warns to be careful when using this product. Another interesting thing that I found from this article was that this reaction occured without a catalyst. The component within the reaction was strong enough to drive it without any extra aid from a catalyst. For some future directions for this paper they could look into ways to help stabilize the product from becoming explosive. This would help make this reaction safer and less unpredictable. Another future direction they could look at is to create a more efficient way to make the product and decrease the time needed for the reaction to occur. A possibility of this could be to look into catalysts that might be able to help speed up the

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