This week in organic chemistry, we were assigned to find a journal with at least one electrophilic aromatic substitution (EAS) step and talk about the step specifically. After much searching, I was able to find an article that did not require me to purchase it. The article is titled "Selective Nitration of Aromatic Compounds with Bismuth Subnitrate and Thionyl Chloride" and is written by Hussni A. Muathen. In part of the article, Muathen talks of how "polycyclic aromatic hydrocarbons can be efficiently mononitrated in good yields. Biphenylene, in particular, afforded 2- nitrobiphenylene as the only product in high yield." The image of this reaction would not let me save it or copy it, so if you would like to view the reaction, you can go to the source below. This nitration is performed very similarly to the nitrations in the book. The only difference between the two is the compound used to make the electrophile (NO2+) in the article is SOCl4 and the one used in the book is H2SO4. These two reagents achieve the same goal. Anyway I found this to be an interesting article and I'm glad I was able to share it. =)
-The High School Chemist
Source
http://www.mdpi.com/1420-3049/8/7/593/pdf
Interesting find. I wonder how they support their claim that "We believe that the nitrate may
ReplyDeletedisproportionate in the more polar dichloromethane to give sulfur dioxide and nitryl chloride (NO2Cl),
which might be the nitrating species." That seems like a stretch to me, perhaps I should read the paper...
First off, I'd simply like to congratuate you on just finding an appropriate article! Ha, I don't know about you, but it sure was tough for me! Overall, I think you did a great job. Especially citing your source and giving credit to the author. Being able to click on the link and view the article really helped me to fully understand what you were describing. I also really liked that you linked how the reaction was performed in the article, with how these types of reactions are shown in the book, and that you stated that though different reagents may be used, the end products are ultimately the same. The only thing I might have added would have been the page numbers (and a source) for Smith, just in case the reader wanted to look up the mechanism in the book.
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