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Issue 7, 2005
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Reactions of 1-haloadamantanes and ethylmercury chloride with nitronate anions by the SRN1 mechanism

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Abstract

Secondary or tertiary nitro compounds can be easily obtained by photostimulated reaction of the anions corresponding to primary or secondary nitroalkanes with either 1-iodoadamantane (1-AdI) or ethylmercury chloride (EtHgCl) by the SRN1 mechanism. Only 1-AdI requires the presence of the enolate anion of acetone as an entrainment reagent. The procedure works well with the nitroanions derived from 1-nitropentane, nitroethane or 6-nitrohex-1-ene, but with 2-nitropropane ion the outcome depends on the substrate and solvent.

Graphical abstract: Reactions of 1-haloadamantanes and ethylmercury chloride with nitronate anions by the SRN1 mechanism

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Publication details

The article was received on 03 Dec 2004, accepted on 02 Feb 2005 and first published on 06 May 2005


Article type: Paper
DOI: 10.1039/B418305C
New J. Chem., 2005,29, 875-880

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    Reactions of 1-haloadamantanes and ethylmercury chloride with nitronate anions by the SRN1 mechanism

    A. N. Santiago, S. M. Basso, C. A. Toledo and R. A. Rossi, New J. Chem., 2005, 29, 875
    DOI: 10.1039/B418305C

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