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Investigation of the full reversal of selectivity in the reaction of aniline with 1,3-dichloro-1,3-bis(dimethylamino)vinamidinium salts

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Abstract

The addition of aniline, even in excess, to a solution of 1,3-dichloro-1,3-bis(dimethylamino)vinamidinium salt in the presence of triethylamine invariably leads to the formation of 2,4-bis(dimethylamino)quinoline. Conversely, delaying the addition of the base leads to the formation of 1,3-dimethylamino-N,N′-diphenylpropane-1,3-diimine, even when only a substoichiometric amount of aniline was used. A DFT study led to the consideration of factors that accounted for this reversal of reactivity. The role of a secondary orbital interaction in key transition states, as well as the role of solvent, is discussed.

Graphical abstract: Investigation of the full reversal of selectivity in the reaction of aniline with 1,3-dichloro-1,3-bis(dimethylamino)vinamidinium salts

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Publication details

The article was received on 11 Sep 2017, accepted on 02 Nov 2017 and first published on 02 Nov 2017


Article type: Paper
DOI: 10.1039/C7NJ03442C
Citation: New J. Chem., 2017, Advance Article
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    Investigation of the full reversal of selectivity in the reaction of aniline with 1,3-dichloro-1,3-bis(dimethylamino)vinamidinium salts

    M. Tripathi, V. Regnier, C. Lincheneau and D. Martin, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ03442C

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