3,3-Diferrocenylcyclopropene

• Published in: Journal of organometallic chemistry 2002-10, Vol.659 (1), p.56-63
• Main Authors: Klimova, Elena I., Garcı́a, Marcos Martı́nez, Klimova, Tatiana, Stivalet, José M.Mendez, Hernández Ortega, Simón, Ramı́rez, Lena Ruı́z
• Format: Article
• Language: English
• Subjects: 3-Membered ring opening; Dehydrohalogenation; Ferrocene; Ferrocenylallylic cation; Ferrocenylcarbenoid; Ferrocenylcyclopropane; Ferrocenylcyclopropene
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/S0022-328X(02)01702-3

Dehydrohalogenation of isomeric 2-chloro- and 2-bromo-1,1-diferrocenylcyclopropanes ( Z- and E-isomers with respect to the ‘bisecting’ ferrocenyl substituent) under the action of Bu t OK in DMSO afforded 3,3-diferrocenylcyclopropene. In solution, this underwent facile opening of the small ring to give 3-ferrocenyl-1 H-cyclopentaferrocene (∼55%) and 1,1-diferrocenylpropene (15%). The spatial structure of Z-2-chloro-1,1-diferrocenylcyclopropane and 1,1-diferrocenylcyclopropane were elucidated by X-ray diffraction analysis of a single crystal. Dehydrohalogenation of isomeric 2-chloro- and 2-bromo-1,1-diferrocenylcyclopropanes ( Z- and E-isomers with respect to the ‘bisecting’ ferrocenyl substituent) under the action of Bu t OK in DMSO afforded 3,3-diferrocenylcyclopropene. In solutions, this underwent facile opening of the small ring to give 3-ferrocenyl-1 H-cyclopentaferrocene (∼55%) and 1,1-diferrocenylpropene (15%). The spatial structure of Z-2-chloro-1,1-diferrocenylcyclopropane and 1,1-diferrocenylcyclopropane were elucidated by X-ray diffraction analysis of a single crystas.