2421-26-3Relevant articles and documents
Infrared studies of conformational isomerism in some gem-chloronitrosoalkanes
Evans, K. M.,Ireson, S. J.,McCoustra, M. R. S.,Pfab, J.
, p. 659 - 670 (1992)
The IR spectra of 2-chloro-2-nitrosopropane, 2-chloro-2-nitrosobutane and 2-chloro-3-methyl-2-nitrosobutane have been studied in the gas phase and solid phase, and in solutions of varying polarity.The spectra reveal clear evidence for the hindered internal rotation of the NO functional group about the C-N bond in a splitting of the N=O stretching band.The spectra can be interpreted as arising from energetically favoured cis conformational isomers, exhibiting the higher of the observed N=O stretching frequencies.In each case, assignment of the lower N=O stretching frequency is uncertain on the basis of experimental evidence.The results of semi-empirical molecular orbital calculations, however, support the assignment of this feature to the gauche conformational isomers.Temperature dependent IR spectroscopy has been employed in the determination of conformational enthalpy differences in both the gas phase and non-polar solution, which are then compared to the results of semi-empirical molecular orbital calculations.
New and improved methods for the conversion of nitroalkanes into geminal chloronitroso compounds
Bou-Moreno, Rafael,Luengo-Arratta, Sandra,Pons, Valerie,Motherwell, William B.
, p. 6 - 12 (2013/03/13)
The scope and limitations of a new method for the preparation of geminal chloronitroso compounds involving treatment of a nitronate anion with oxalyl chloride are described in full, and a milder, high yielding, and more chemoselective variant using the de
Nouvelles donnees sur la reaction entre le chlorure de pyridinium et les nitroalcanes. Cas du nitro-2 propane
Dauzonne, Daniel,Demerseman, Pierre,Royer, Rene
, p. 204 - 206 (2007/10/02)
We have previously established that a refluxing mixture of a pyridinium halide and a primary nitroalcane gives rise to unexpected electrophilic halogenation of activated aromatic compounds with good yield (1).We confirm here that such unusual halogenation can be performed by means of pyridinium chloride and 2-nitropropane.Thus, when refluxing these two latter reagents in the presence of 2-methoxynaphtalene 1, 60percent of 1-chloro-2-methoxynaphtalene 2 is formed.However, the other products of the reaction (nitrogen oxides, 2-chloro-2-nitrosopropane 3, anetone and acetone oxime) are different from those formed with nitroethane (1-acetylpyridinium chloride oxime, acetohydroxamic acid, acetonitrile, acetamide, acetic acid and ammonium chloride).Although their results are notably different, both transformations induced respectively by the primary or the secondary nitroalcane start with the formation of a protonated nitronic acid and proceed according to similar mechanisms, as a consequence of the nucleophilic attack of the aci-nitro intermediate, among others, by the chloride anion.
