Synthesis and some chemical properties of 3-ferrocenyl-3-isopropylcyclopropene: 3-ferrocenyl-3-isopropylstructures of cyclopropene and its adducts with 1,3-diphenylisobenzofuran

X-ray structural analysis allowed the molecular conformation of 3-ferroceny l-3-isopropylcycloyropene to be established, where the ferrocenyl fragment occupies a bisecting position relative to the three-membered ring. Some het erolytic cleavage of a sigma C-C bond in cyclopropene was observed. As a re sult, predominantly linear products are formed: 1,1-dimethyl-2-ferrocenyl-1 ,3-butadiene, 3-ferrocenyl-4-methyl-2-pentene, 3-ferrocenyl-4-methyl-3-pent enine and also 3-isopropyl-1H-cyclopentaferrocene. Cyclopropene forms a cla ssical Diels-Alder adduct with 1,3-diphenylisobenzofuran and an adduct with the intermediate 3-isopropyl-1,2-(1-propene-1,3-diyl)ferrocene. X-ray stru ctural data of exo-1,5-diphenyl-3-anti-ferrocenyl-3-syn-isopropyl-6,7-benzo -8-oxatricyclo[3.2. 1.0(2,4)]oct-6-ene are presented. (C) 2000 Elsevier Sci ence S.A. All rights reserved.