Preparative Organic Chemistry
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ChemInform Abstract: An Example of an Unusual Smiles Rearrangement.
First published: September 22, 1987
Abstract
N-(2,4,6-Trinitrophenyl)ethylenediamine (III), which is prepared from picryl chloride (I) and ethylenediamine (II), on reaction with nitrating acid followed by aqueous work-up affords the product (V), which is probably formed by Smiles rearrangement of the intermediate (IV).
ChemInform Abstract
N-(2,4,6-Trinitrophenyl)ethylenediamine (III), which is prepared from picryl chloride (I) and ethylenediamine (II), on reaction with nitrating acid followed by aqueous work-up affords the product (V), which is probably formed by Smiles rearrangement of the intermediate (IV). This is confirmed by 1H NMR examination of a solution of (III) in N2O5/D2SO4.
