Synthesis of ‘three-petal’ carbocyclic systems based on s- cis-diferrocenyltrienes

• Published in: Journal of organometallic chemistry 2002-04, Vol.649 (1), p.86-93
• Main Authors: Klimova, Elena I., Martı́nez Garcı́a, Marcos, Klimova, Tatiana, Alvarez Toledano, Cecilio, Alfredo Toscano, Ruben, Ruı́z Ramı́rez, Lena
• Format: Article
• Language: English
• Subjects: Ferrocene; Fragmentation; Homoannular alkylation; s- cis-Diferrocenyltrienes; Spirocyclodimers; X-ray diffraction analysis
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/S0022-328X(02)01127-0

Acid-catalyzed intramolecular, homoannular alkylation of one of the ferrocenyl substituents in spirocyclodimers derived from 1,3-bis(ferrocenylmethylidene)-2-methylidene-cyclohexane, -cycloheptane, and 3,5-bis(ferrocenylmethylidene)-4-methylidene- N-methylpiperidine results in a fused system with a ‘three-petal’ moiety in the center. The structure of 1-ferrocenyl-3,11-bis(ferrocenylmethylidene)-2,3,4,5,6,6b,10,10a,11,12,13,14-dodecahydro-1 H-benzo[ d](ferroceno[ a])phenanthrene was established by X-ray diffraction analysis. Acid-catalyzed intramolecular, homoannular alkylation of one of the ferrocenyl substituents in spirocyclodimers derived from 1,3-bis(ferrocenylmethylidene)-2-methylidene-cyclohexane, -cycloheptane, and 3,5-bis(ferrocenylmethylidene)-4-methylidene- N-methylpiperidine results in a fused system with a ‘three-petal’ moiety in the center. The structure of 1-ferrocenyl-3,11-bis(ferrocenylmethylidene)-2,3,4,5,6,6b,10,10a,11,12,13,14-dodecahydro-1 H-benzo[ d](ferroceno[ a])phenanthrene was established by X-ray diffraction analysis.