Jump to main content
Jump to site search

Issue 24, 2017
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

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., 2017,41, 15016-15020
  •   Request permissions

    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, 41, 15016
    DOI: 10.1039/C7NJ03442C

Search articles by author

Spotlight

Advertisements