Synthesis, Structure, and Some Chemical Properties of Diferrocenyl-1,2,3-triazines

The reactions of 1-amino-2,3-diferrocenylcyclopropenylium tetrafluoroborate (5a-c) or 2,3-diferrocenyl-l-methylthiocyclopropenylium iodide with sodium azide afford 5-methylthino-4,6-diferrocenyl-1,2,3-triazines (7a-c) or 5-methylthio-4,6-diferrocenyl- and 4-methylthio-5,6-diferrocenyl-1,2,3-triazines (8a and 8b), respectively. Their structures were established using spectroscopic methods and that of compound 8a was confirmed using X-ray diffraction analysis. Triazines 5a-c react with alkyl iodides to yield N(2)- and N-alkyl-C(5)-derivatives. Their alkaline hydrolysis results in 2-methyl-4,6-diferrocenyl-2,5dihydro-1,2,3-triazin-5-one (16) and 4,6-diferrocenyl-5-hydroxy-1,2,3-triazine (17).