The synthesis of a new N-heterocyclic carbene with bulky S-arylthiocarbamate substituents was devised from the condensation between 2-chloromethyl-4-methy-l,6-[3,5-bis(trifluoromethyl)-phenyl]-S-phenyl-N,N-dimethylthiocarbamate and imidazole, resulting in the proligand N,N’-bis[(2-S-(N’’,N’’-dimethylthiocarbamoyl)-5-methyl)phenylmethyl]imidazolium iodide [H(S-carb)2NHC]I. This newly synthesized proligand was crystallographically characterized, thus confirming its identity; its stability was established in several solvents, resulting in air oxidation in methanolic solution, giving rise to the decomposition product N,N’-bis[(2-S-(N’’,N’’-dimethyl thiocarbamoyl)-5-methyl)phenylmethyl]-4,5-dimethoxyimidazolyl-2-one. Reaction of the proligand with silver oxide afforded the corresponding complex [(S-carb)2NHC]AgI, which was fully characterized by spectroscopic techniques.

Diferrocenyl(methylthio)cyclopropenylium iodide reacts with nitro compounds as CH-acids in the presence of triethylamine to yield both products with retention of the three-carbon ring and ring-opening products. Thus, 4-(4-nitrobenzyl)pyridine affords 1,2-diferrocenyl-3,3-dimethylthio- and 1,2-diferrocenyl-3-[(4-nitrophenyl)(4-pyridyl)methylidene]cyclopropenes and acyclic compounds: 2,3-diferrocenyl-1,3,3-tris(methylthio)propene and 2,3- diferrocenyl-1-methylthio-4-(4-nitrophenyl)-4-(4-pyridyl)buta-1,3-diene. Their structures were established based on data from ¹H and 13C NMR spectroscopy and X-ray diffraction analysis. The mechanistic aspects of these reactions are discussed.

El yoduro de diferrocenil(metiltio)ciclopropenilo reacciona con los nitro-compuestos como CH-ácidos en presencia de trietilamina formándose los productos con la retención del anillo de tres miembros y con apertura del mismo. De esta manera, la 4-(4-nitro-bencil)piridina produce los 1,2-diferrocenil-3,3-dimetiltio- y 1,2-diferrocenil-3-[(4-nitrofenil)(4-piridil)metiliden]ciclopropenos, así como los compuestos acíclicos: 2,3-diferrocenil-1,3,3-tris(metiltio)propeno y 2,3-diferrocenil-1-metiltio-4-(4-nitrofenil)-4-(4-piridil)buta-1,3-dieno. Sus estructuras fueron establecidas con base a la espectroscopia de RMN ¹H y de 13C además de un análisis de difracción de rayos X. Se discuten los aspectos mecanísticos de estas reacciones.