The Chemistry of Tetranitromethane

Specificity of the Reaction of Tetranitromethane with Alkenes in Nitromethane

“…An analogous behavior was described previously for some olefins having bulky substituents [14]. In the reaction of tetranitromethane with sterically unhindered alkenes, [2 + 3]-cycloaddition of nitronate E to the substrate leads to isoxazolidine derivatives H [1][2][3][4][5][6][7][8].…”

“…Reactions of tetranitromethane with alkenes have been the subject of numerous studies [1][2][3]. According to published data, tetranitromethane reacts with olefins to afford, depending on the substrate structure, 3,3-dinitroisoxazolidines, tetranitropropanes, nitroalkenes, or α-nitro ketones [1].…”

Unusual reactions of vinyl ketones with tetranitromethane. The synthesis of 5-acyl-3-nitroisoxazoles

“…The mechanism of this reaction will be a subject of our further investigations. 1 H and 13 C NMR spectra were recorded on a Bruker AM 400 spectrometer (400 and 100 MHz, respectively) in CDCl 3 with chloroform as the internal standard (δ H 7.28 and δ C 77.1). The course of the reactions was monitored and the purity of the products was checked by TLC on Silufol UV 254 plates.…”

Polynitromethanes - Unique Reagents in the Synthesis of Nitro-Substituted Heterocycles

“…4 The first survey focusing on the chemistry of tetranitromethane (TNM) was published in 1976. 5 In addition, monographs that describe transformations of acyclic nitronates generated from polynitromethanes appeared during 1980-2002. 6 The latest review on the chemistry of nitronates was published in 2008.…”