Polyhalogenoheterocyclic compounds. Part 39. Reactions of 4,5,6-tris(perfluoroisopropyl)-1,2,3-triazine involving nucleophilic attack at heterocyclic nitrogen. X-Ray crystal structure of a spiro triazinium zwitterion

Abstract

Reactions of 4,5,6-tris(perfluoroisopropyl)-1,2,3-triazine (1) with phenylmagnesium bromide and a range of electron-rich alkenes and dienes are described. Reactions result in addition onto the 1,2,3-triazine system by nucleophilic attack at N-2. Phenylmagnesium bromide and triazine (1) yield 2-phenyl-1,2,3-triazine derivative (3); reactions of (1) with dimethylbutadiene and isoprene yield the spirotriazinium zwitterion structures (5a–c). 2,3-Dimethylbut-2-ene and 2-methylbutene react with triazine (1) to give the N-substituted triazines (9a) and (9b), respectively. X-Ray crystal analysis reveals that the triazine ring of adduci (5a) adopts an eclipsed boat conformation.