Aminolysis of 2-X-4,6-diphenyl-l,3,5-Triazines

A more detailed investigation of the amination of 2-chloro-4,6-diphenyl-[(l),(3),(5)- N]l,3,5-triazine (135, A = Cl) revealed that the participation of the Sn(ANRORC) mechanism is strongly dependent on the potassium amide/substrate ratio (see Table II.ll) (76RTC113). 

The data in Table II.ll show that the participation of the Sn(ANRORC) mechanism decreases with decreasing potassium amide/substrate ratio. When no potassium amide is present, the participation of the ANRORC mechanism is zero and the aminolysis occurs according to the Sn(AE) mechanism. Apparently in the amination of the highly 77-electron-deficient 1,3,5-triazines, a competition is involved between the strong nucleophilic amide ion, which leads via a-adduct 136 and the ring-opened compound 137 to product 2-[ N-amino]-4,6-diphenyl-l,3,5-triazine, and the weaker nucleophile liquid ammonia, which replaces by an Sn(AE) process the 

The Percentage of Sn(ANRORC) Participation in THE Aminolysis of 2-Chloro-4,6-diphenyl[ N] 1,3,5-Triazine in Dependency on the Potassium Amide/Substrate Ratio 

---