Investigation of the full reversal of selectivity in the reaction of aniline with 1,3-dichloro-1,3-bis(dimethylamino)vinamidinium salts
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[prime or minute]-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.
Références
- Titre
- Investigation of the full reversal of selectivity in the reaction of aniline with 1,3-dichloro-1,3-bis(dimethylamino)vinamidinium salts
- Type de publication
- Article de revue
- Année de publication
- 2017
- Auteurs
- Tripathi, Monika, Regnier Vianney, Lincheneau Christophe, and Martin David
- Revue
- New J. Chem.
- Volume
- 41
- Pagination
- 15016-15020
Soumis le 6 juin 2018