4-(4-Nitrobenzyl)pyridine in Reaction with Diferrocenyl(methylthio)cyclopropenylium Iodide
DOI:
https://doi.org/10.29356/jmcs.v51i1.1334Keywords:
Ferrocene, cyclopropenylium iodide, cyclopropenes, diferrocenyl-1,3-butadieneAbstract
Abstract. 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 ringopening 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.
Resumen. 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-nitrobencil) 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.
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