Issue 7, 2005

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

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

Article information

Article type
Paper
Submitted
03 Dec 2004
Accepted
02 Feb 2005
First published
06 May 2005

New J. Chem., 2005,29, 875-880

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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