Tri-s-TRIAZINE: SYNTHESIS, CHEMICAL BEHAVIOR, AND SPECTROSCOPIC AND THEORETICAL PROBES OF VALENCE ORBITAL STRUCTURE.

Article abstract of DOI:10.1021/ja00322a014

The synthesis, physical properties, and chemical properties of unsubstituted tri-s-triazine (1,3,4,6,7,9,9b-hepta-azaphenalene) are reported. 2,4-diamino-1,3,5-triazine was treated with methyl N-cyanomethanimidate and NaOMe in Me//2SO/MeOH to give 2,4-bis(N prime -cyano-N-formamidino)-1,3,5-triazine, which was subjected to short vacuum pyrolysis to give tri-s-triazine. The compound gave no evidence of (a) formation of pi complexes with either electron-donor or electron-acceptor organic partners, (b) protonation, (c) alkylation, or (d) N-oxidation, yet it formed complexes with silver salts and decomposed in water. Photoelectron spectroscopic studies of tri-s-triazine have provided ionization potentials associated with the six highest occupied pi and six highest occupied lone-pair orbitals.