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Issue 6, 2013
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A further study of acetylacetone nitrosation

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The nitrosation of acetylacetone (AcAc) has been revised in an aqueous acid medium of perchloric acid and buffers of mono-, di-, or tri-chloroacetic acid. The results show that in the presence of buffers, under conditions of [nit] ≪ [AcAc] (nit = sodium nitrite) the reaction cannot be studied by UV-Vis spectroscopy, contrary to the recently published paper by García-Rio et al. (J. Org. Chem., 2008, 73, 8198). The present study also corroborates the previously published mechanism of AcAc nitrosation, where no base-catalysis was observed. Contrarily, the low effect of buffers was attributed to the formation of nitrosyl chloro-, dichloro- or trichloro-acetate salts that are new nitrosating agents.

Graphical abstract: A further study of acetylacetone nitrosation

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The article was received on 04 Jun 2012, accepted on 25 Jul 2012 and first published on 03 Jan 2013

Article type: Paper
DOI: 10.1039/C2OB26073E
Org. Biomol. Chem., 2013,11, 1059-1064

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    A further study of acetylacetone nitrosation

    E. Iglesias and I. Brandariz, Org. Biomol. Chem., 2013, 11, 1059
    DOI: 10.1039/C2OB26073E

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