Abstract
Decomposition of N-cyclopropyl-N-nitrosourea under the action of K2CO3 or KOH containing 15—20% of H2O at 0—7 °C gives rise to cyclopropyldiazonium, which reacts with some β-diketones, methyl cyanoacetate, or malonodinitrile to form the corresponding cyclopropylhydrazones. The latter compounds are analogous to products of azo coupling and isomerization of aryldiazonium ions with the above-mentioned substrates. These transformations provide the first example of azo coupling of the cyclopropyldiazonium ion in the series of activated aliphatic CH acids.
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Tomilov, Y.V., Kostyuchenko, I.V., Shulishov, E.V. et al. Formation of N-cyclopropylhydrazones by azo coupling of cyclopropyldiazonium with aliphatic CH acids. Russian Chemical Bulletin 52, 993–997 (2003). https://doi.org/10.1023/A:1024429232345
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DOI: https://doi.org/10.1023/A:1024429232345