This article is cited in 21 papers

Reactivity of the low-nucleophilic N-dinitromethyl carbanion center in polynitromethylazoles

V. V. Semenov, S. A. Shevelev

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: Reactivity of N-dinitromethylazoles possessing extremely high CH acidity (pK_a –1.75–0) was investigated in Michael, Henry and alkylation reactions. N-Dinitromethylazole K-salts and hexamethylenetetramine under acidic conditions yield bis-Mannich bases (86–100%) whose secondary amine moiety can be N-nitrated with HNO₃–H₂SO₄ system.

Language: English

DOI: 10.1016/j.mencom.2010.11.010

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