2.4.6- Tricyano-1,3,5-triazine

A new class of heteroaromatic compound was introduced by the synthesis of a diphosphathienoquinone (20). It can be reduced to a semiquinone radical anion and dianion at lower potentials than phosphaalkenes. The ESR spectrum indicates that the two P atoms are not equivalent213. 2,4>6-Tricyano- 1,3,5-triazine undergoes dimerization to yield 4,4, 6,6 -tetracyano-2,2 -bitriazine214. 

Tricyano- -triazine (322) is mono-substituted very rapidly with anhydrous methanol (20°, few min) and with water di- and trisubstitution products also result under mild conditions (65°, one min, and 65°, several hr, respectively, for methanol). 

These compounds are thermally stable. 2,4,6-Tricyano-l,3,5-triazine reacts rapidly with water to form cyanuric acid and hydrogen cyanide (equation 12) (59HC(13)1, p.170). 

Recent work has shown that in cases where the silylated amidines are not readily accessible, e.g., tricyano-sym-triazine 82 (where addition of Li[N(SiMe3)2] leads to nucleophilic attack at the triazine carbon atoms (93IC1554)), this route may be utilized instead. 

Chemical reduction of 2,4,6-tricyano-l,3,5-triazine, TCYT, results in the formation of an unstable radical anion that undergoes immediate dimerization at a ring carbon to form [Gi2Ni2], [TCYT]2, characterized by a long... 

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