3457-58-7Relevant articles and documents
Metal-Free C-Arylation of Nitro Compounds with Diaryliodonium Salts
Dey, Chandan,Lindstedt, Erik,Olofsson, Berit
, p. 4554 - 4557 (2015/09/28)
An efficient, mild, and metal-free arylation of nitroalkanes with diaryliodonium salts has been developed, giving easy access to tertiary nitro compounds. The reaction proceeds in high yields without the need for excess reagents and can be extended to α-arylation of nitroesters. Nitroalkanes were selectively C-arylated in the presence of other easily arylated functional groups, such as phenols and aliphatic alcohols.
An efficient nitration of light alkanes and the alkyl side-chain of aromatic compounds with nitrogen dioxide and nitric acid catalyzed by N-hydroxyphthalimide
Nishiwaki, Yoshiki,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 5663 - 5668 (2007/10/03)
Nitration of light alkanes and the alkyl side-chain of aromatic compounds with NO2 and HNO3 was successfully achieved by the use of N-hydroxyphthalimide (NHPI) as a catalyst under relatively mild conditions. For example, the nitration of propane with NO2 catalyzed by NHPI at 100 °C for 14 h gave 2-nitropropane in good yield without formation of 1-nitropropane and cleaved products such as nitroethane and nitromethane. Various aliphatic nitroalkanes, which are difficult to prepare by conventional methods, could be selectively obtained by means of the present methodology by using NHPI as the key catalyst. In addition, the side-chain nitration of alkylbenzenes such as toluene was selectively carried out to lead to α-nitrotoluene without the ring nitration. The present reaction provides an efficient selective method for the nitration of light alkanes and alkylbenzenes, which has been very difficult to carry out so far.
Mechanisms in the reaction of arenediazonium cations with 2-nitropropanide anion
Khanna, Rajive K.,Jiang, Yong M.,Singh
, p. 5449 - 5452 (2007/10/02)
Lithium 2-nitropropan-2-ide reacts, in MeOH solvent, with benzenediazonium and p-methoxybenzenediazonium cations to give diazo-coupled products, but with p-nitrobenzenediazonium cation by competing electron transfer and diazo-coupling reactions.