595-42-6Relevant academic research and scientific papers
Reactions of 1-haloadamantanes and ethylmercury chloride with nitronate anions by the SRN1 mechanism
Santiago, Ana N.,Basso, Silvana M.,Toledo, Carlos A.,Rossi, Roberto A.
, p. 875 - 880 (2007/10/03)
Secondary or tertiary nitro compounds can be easily obtained by photostimulated reaction of the anions corresponding to primary or secondary nitroalkanes with either 1-iodoadamantane (1-AdI) or ethylmercury chloride (EtHgCl) by the SRN1 mechani
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.
Kinetic studies of the reaction of some nitrosoalkanes with nitrogen dioxide
Gowenlock, Brian G.,King, Boyd,Pfab, Josef,Witanowski, Michal
, p. 483 - 485 (2007/10/03)
The rates of the oxidation of some nitrosoalkanes (CH3)2C(CH2X)NO by nitrogen dioxide in carbon tetrachloride have been studied by stopped-flow techniques, and have been found to exhibit second order kinetics. Arrhenius parameters have been determined for the cases of X = H, CH3, C(CH3)3, C6H5, NO2, Cl and OCOCH3. Electron withdrawing substituents are found to decrease significantly the rates, which are generally much faster than the corresponding oxidation of nitrosoarenes. The results obtained are discussed with reference to the Hammett σ constants of the substituents X, and the atomic charges at the nitrogen atom as given by the TNDO/2 method, the geometries of the molecules having been optimised by the PM3 semi-empirical method.
