Reverdin reaction
The Reverdin reaction (also Reverdin rearrangement ) is a name reaction from the field of organic chemistry. It is named after the Swiss chemist Frédéric Reverdin (1849–1931).
The nitration of 4-iodoanisole with rearrangement of the iodine group is known as the Reverdin reaction . The product is a 2-iodo-4-nitroanisole.
mechanism
The following reaction mechanism is proposed for the reaction:
First, a nitronium ion is formed from two equivalents of nitric acid . In the next step, the nitronium ion displaces the iodine cation at the para position of the anisole by electrophilic aromatic substitution . In the next step, the iodine cation is also deposited in the ortho position by means of electrophilic aromatic substitution, which creates the product. It is also assumed that 2,4-diiodanisole is also formed in addition to the end product . However, through renewed nitration in the para position, the end product would also result from this.
Individual evidence
- ↑ Reverdin, F .: About some iodine derivatives of anisole and about a case of migration of the iodine atom . In: Reports of the German Chemical Society . 29, No. 1, 1896, pp. 997-1005. doi : 10.1002 / cber.189602901190 .
- ↑ Reverdin, F .: About the migration of the iodine atom in the anisole and phenetole derivatives . In: Reports of the German Chemical Society . 29, No. 3, 1896, pp. 2595-2599. doi : 10.1002 / cber.18960290338 .
- ↑ Alexander Senning: Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology . Elsevier, 2006, ISBN 978-0-08-048881-3 , pp. 339 ( books.google.de ).
- ↑ a b Z. Wang (Ed.): Comprehensive Organic Name Reactions and Reagents, 3 Volume Set . John Wiley & Sons, Hoboken, New Jersey 2009, pp. 2382-2384, ISBN 978-0-471-70450-8 .
- ↑ a b Robinson, GM: Experiments on the so-called migration of atoms and groups. Part I. The nitration of p-iodoanisoles and other iodo-phenolic ethers . In: J. Chem Soc Trans... . 109, 1916, pp. 1078-1091. doi : 10.1039 / CT9160901078 .