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Direct Aziridination of Nitroalkenes Affording N-Alkyl-C-nitroaziridines and the Subsequent Lewis Acid Mediated Isomerization to β-Nitroenamines

“…Due to their “push–pull” property, β-nitroenamines serve as key synthetic intermediates for functional materials such as bioactive compounds and optical materials . However, very few reports are focused on β-aryl-β-nitroenamines because of their poor availability . Therefore, our method potentially yields a novel class of β-nitroenamines with structural diversity.…”

“…This mechanism is consistent with the fact that nitroenamines possessing an electron-rich aromatic group were efficiently obtained. In this step, the ( Z )-isomer was mainly formed due to the stabilization by an intramolecular hydrogen bond. , …”

Pull‐Pull Alkenes in the Aza‐Michael Reaction

“…So, in this case the direction of the nucleophilic attack is determined by nitro (not sulfonyl) group. In continuation of this work, Russian chemists described later other examples of similar transformations [116,117] …”

Reactions of 1,2-dinitro- and 1-nitro-2-sulfonylethenes with some binucleophiles

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SHORT COMMUNICATIONSThe presence in dinitroethene and nitrosulfonylethene molecules of a strong electron-withdrawing and nucleofugal substituent in the β-position with respect to the conjugated nitro group determines high reactivity of these compounds toward nucleophilic reagents and is responsible for predominant formation of replacement products in such reactions [1][2][3]. We previously reported on the reactions of dinitro-and nitrosulfonylethenes with such difunctional nucleophiles as hydrazine [4], thiourea, and N,N′-diphenylthiourea [5].

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“…UV spectrum (CHCl 3 ): λ max 1360 nm] [6]. The spectral parameters of compounds XII and XIV were typical of nitro enamines [3]. added to a suspension of 0.257 g (1 mmol) of compound V in 10 ml of ethanol.…”