207462-98-4

Upstream product

• 207462-86-0 3-ferrocenyl-3-(1-naphthyl)cyclopropene 
• 5471-63-6 1,3-diphenylisobenzofuran 

Downstream Products

• 214823-13-9 (C₅H₅)Fe(C₅H₄(C₂₃H₁₆NO₂)) 
• 214823-11-7 (C₅H₅)Fe(C₅H₄(C₂₁H₁₄N₃O₂)) 

Relevant academic research and scientific papers

3-ferrocenyl-3-(1-naphthyl)cyclopropene. Synthesis, structure, and chemical transformations

Crystalline 3-ferrocenyl-3-(1-naphthyl)cyclopropene was prepared by dehydrobromination of Z- and E-2-bromo-1-ferrocenyl-1-(1-naphthyl)-cyclopropanes by ButOK in DMSO. The resulting compound and the starting Z-monobromocyclopropane were characterized by X-ray diffraction analysis. The obtained cyclopropene reacts with 1,3-diphenylisobenzofuran to give a [4+2|-cycloadduct. The small ring opens upon treatment with HBF4 etherate to afford isomeric Z- and E-prop-1-enes and 1-ferrocenyl-3H-benzo[e]indene. Thermolysis of this cyclopropene results in the formation of 1-ferrocenyl-9bH-benzo[e]indene. In all cases, opening of the small ring is accompanied by exclusive alkylation of the naphthalene moiety.

Regioselectivity of alkylation of the naphthalene fragment in the opening of a small ring in 3-ferrocenyl-3-(1-naphthyl)cyclopropene, Z-2-bromo-1-ferrocenyl-1-(1-naphthyl)cyclopropane, and 1-ferrocenyl-1-(1-naphthyl)cyclopropane

The opening of a small ring in 3-ferrocenyl-3-(1-naphthyl)cyclopropene (thermolysis, action of HBF4·Et2O or CF3SO3H), Z-2-bromo-1-ferrocenyl-1-(1-naphthyl)cyclopropane (action of AlCl3), and in 1-ferrocenyl-1-(1-naphthyl)cyclopropane (action of Ph3C+BF4-) is accompanied by the alkylation of only the naphthalene fragment giving rise to 1-ferrocenyl-9bH-benzo[e]indene or 1-ferrocenyl-3H-benzo[e]indene. This is connected with a 'non-bisecting' position of the naphthalene fragment relative to the three-membered cycle in the starting compounds. The compound 1-ferrocenyl-9bH-benzo[e]indene gives [4+2]-cycloadducts with N-phenyl(azodicarboximide) and N-phenylmaleimide. X-ray structural data are presented for 3-ferrocenyl-3-(1-naphthyl)cyclopropene and its adduct with 1,3-diphenylisobenzofuran, Z-2-bromo-1-ferrocenyl-1-(1-naphthyl)cyclopropane, and 1-ferrocenyl-1-(1-naphthyl)cyclopropane.