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

Abstract magnified image 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).