1,2,4-Triazines X: Dimerizations of 1,2,4-triazmes

5,5′-Bi-1,2,4-triazinyl compounds are obtained by the treatment of 5-unsubstiluted 1,2,4-triazines with either sodium methoxide or with aqueous potassium cyanide. 5,5′-Bi-1,2,4-triazinyl is also obtained by the reaction of 1,2,4-triazine with potassium cyanide. It is proposed that the sodium methoxide catalyzed dimerizations occur via a carbanionic intermediate; the aqueous potassium cyanide catalyzed reactions via a cyanide addition product and the potassium in liquid ammonia reaction via a free radical dimerization process.