Synthesis, structure, and some chemical properties of diferrocenyl‐1,2,3‐triazines

The reactions of 1‐amino‐2,3‐diferrocenylcyclopropenylium tetrafluoroborate ( 5a , 5b , 5c ) or 2,3‐diferrocenyl‐1‐methylthiocyclopropenylium iodide with sodium azide afford 5‐amino‐4,6‐diferrocenyl‐1,2,3‐triazines ( 7a , 7b , 7c ) 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 , 5b , 5c react with alkyl iodides to yield N(2)‐ and N‐alkyl‐C(5)‐derivatives. Their alkaline hydrolysis results in 2‐methyl‐4,6‐diferrocenyl‐2,5‐dihydro‐1,2,3‐triazin‐5‐one ( 16 ) and 4,6‐diferrocenyl‐5‐hydroxy‐1,2,3‐triazine ( 17 ). J. Heterocyclic Chem., 46, 477 (2009).