G. Simig, H. Plas, C. Landheer
Sep 2, 2010
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
Amination of 2-X-4, 6-diphenyl-1,3,5-triazines (X = H, Cl, SCH3) with KNH2 in liquid NH3 at −33° yields 2-amino-4, 6-diphenyl-1,3,5-triazine. 2-Chloro-4, 6-diphenyl-1,3,5-triazine can also be aminated by liquid NH3 at −33° to give the corresponding 2-amino compound. It is proved using 15N-labelled triazines that i. the amination of 2-(methylthio)-4,6-diphenyl-1. 3,5-triazine proceeds to the extent of about 100% by an SN (ANRORC) mechanism; ii. the amination of 2-chloro-4,6-diphenyl-1,3,5-triazine with liquid NH3 and of 2,4-diphenyl-1,3,5-triazine with KNH2 occurs by an Sn(AE) process; iii. both mechanisms occur in the amination of 2-chloro-4,6-diphenyl 1,3,5-triazine with KNH2 in liquid NH3, the ratio depending on the KNH2 concentration. PMR-spectroscopic evidence is presented for a covalent addition of the amide ion at C-6 of 2,4-diphenyl 1,3,5-triazine.