Molbank 2004

Molbank 2005, M403

http://www.mdpi.net/molbank/

1,1-Dicyanovinyl-2-ferrocene

Abdullah Mohamed Asiri

Chemistry Department, Faculty of Science, King Abdul-Aziz University,

Jeddah 21413, P.O. Box 9028, Saudi Arabia.

Tel. (+966)-2-6952293, Fax (+966)-2-6952293, e-mail: [email protected]

Received: 14 April 2004 / Accepted: 15 April 2004 / Published: 1 July 2005

Key Word: ferrocen, knovenagel condensation, dyes, dicyanomethylene

To a refluxed solution of ferrocenecarboxaldehyde 1 (2.14g, 0.01 mol) and malononitrile 2 (0.66g, 0.01 mmol) in ethanol (25 ml), Piperidine (1 ml) was added. After the addition, the solution became darker and the reflux was continued for six hours, then the solution was left to cool to room temperature and the products were precipitated. The precipitates were filter and washed with cold water and finally with ethanol, dried and recrystallized from ethanol to give the title compound 3. Deep red crystal (1.31g, 50%).

Melting point: 231-233 °C (uncorrected).

UV (EtOH; λ_max nm; ε dm³.mol^-1.cm^-1): 345 (16376); 395 (4945); 521 (4913).

IR (KBr, cm^-1): 2185, 2170 (CN); 1630 (C=C); 1101, 992, 814.

¹H-NMR (400 MHz; CDCl₃): δ= 7.70 (s, 1H, -CH=C); 5.01 (broad s, 2H, H-2, H4, H-5); 4.85 (broad s, 2H, H-2, H3, H-4); 4.33 (s, 5H, C₅H₅).

Elemental Analysis: Calculated for C₁₄H₁₀N₂Fe (262.16): C 64.18%; H 3.82%; N 10.68%; Found; C 64.06%; H 4.01%; N 10.49%.

References

1. S. Barlow, H. E. Bunting, C. Ringham, J. C. Green, G. U. Bublitz, S. G. Boxer, J. W. Perry, S. R. Marder, J. Am. Chem. Soc. 1999; 3715-3718 (121).

Abdullah Mohamed Asiri

2. A. M. Asiri, Appl. Organometal. Chem., 2001, 907-915 (15).