214823-17-3Relevant academic research and scientific papers
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
Klimova, Elena I.,Martinez Garcia, Marcos,Klimova, Tatiana,Alvarez Toledano, Cecilio,Ruben Toscano, Alfredo,Moreno Esparza, Rafael,Ruiz Ramirez, Lena
, p. 175 - 185 (1998)
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.
