Ferrocene 8
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General References, in addition to those in "Eisen-Organische "Eisen-Organische "Eisen-Organische "Eisen-Organische "Eisen-Organische "Eisen-Organische
Verbindungen" Verbindungen" Verbindungen" Verbindungen" Verbindungen" Verbindungen"
A A A A A A
Ferrocen Ferrocen Ferrocen Ferrocen Ferrocen Ferrocen
1, 2, 4, 5, 6, 7,
1974, 1977, 1980, 1981, 1977, 1980,
pp. 2/5, p. 1, p. 1, p. 1, p. 1, pp. 1/2, are:
D. Astruc, Organo-Iron Complexes of Aromatic Compounds. Applications in Synthesis, Tetrahedran 39 [1983] 4027/95. P. N. Gaponik, A. I. Lesnikovich, Yu. G. Orlik, Heterometallic Ferrocene-Based Transition Metal Compounds, Usp. Khim. 52 [1983] 294/320; Russ. Chem. Rev. 52 [1983]168/83. E. G. Perevalova, M. D. Reshetova, K. I. Grandberg, Metody Elementoorganicheskoi Khimii: Zhelezoorganicheskie Soedineniya: Ferrotsen [Methods of Organemetallic Chemistry: Organoiron Compounds: Ferrocene], Nauka, Moscow 1983, pp. 1/544. E. R. Milaeva, A. Z. Rubezhov, A. I. Prokof'ev, 0. Yu. Okhlobystin, Unpaired Electron in Transition Metal Complexes, Usp. Khim. 51 [1982] 1638/73; Russ. Chem. Rev. 51 [1982] 942/60. A. N. Nesmeyanov et aL, Ferrocene and Related Compounds, Nauka, Moscow 1982, pp. 1/439. I. Omae, Organemetallic lntramolecular-Coordination Compounds Containing a Cyclopentadienyl Donor Ligand, Coord. Chem. Rev. 42 [1982] 31/54. S. P. Solodovnikov, lnvestigation of Paramagnetic Metallocenes and Diarene Complexes of Transition Metals by Magnetic Resonance Methods, Usp. Khim. 51 [1982]1674/97; Russ. Chem. Rev. 51 [1982] 961/74. W. R. Cullen, J. D. Woollins, Ferrocene-Containing Metal Complexes, Coord. Chem. Rev. 39 [1981] 1/30.
J. C. Green, Gas Phase Photoelectron Spectra of d- and f-Block Organemetallic Compounds, Struct. Bonding [Berlin] 43 [1981] 37/112. G. B. Shul'pin, Diastereotopy in Transition Metal Complexes, Usp. Khim. 49 [1980]1214/33; Russ. Chem. Rev. 49 [1980] 645/54. R. E. Bozak, Photochemistry in the Metallocenes, Advan. Photochem. 8 [1971] 227/44. Annual surveys are published in J. OrganomataL Chem. and in OrganomataL Chem.; see also Advan. OrganomataL Chem. and OrganomataL Chem. Rev. Gmelin Handbock Fe·Org. Gomp. A 8
M. Drößmar-Wolf, Fe Organoiron Compounds Part A Ferrocene 8 © Springer-Verlag Berlin Heidelberg 1985
2 5.2.3.5
5.2.3.5 Ketones
5.2.3.5.1
1,1'-Compounds
5.2.3.5.1.1 5.2.3.5.1.1.1
1,1'-Diacetylferrocene Fe(C5 H4 -CO-CH 3) 2 Formation and Preparation
From Ferrocene by the Frledel-Crafts Method. For generat information regarding this method see "Ferrocene" 1, 1974, p. 142 ff. and "Ferrocene" 2, 1977, p. 181 ff. The industrial preparation is effected with CH 3COCVAICI3 [34].In the laboratory the acetylation is conducted predominantly by stepwise addition of ferrocene in CH 2CI2 to a mixture of CH 3 COCVAICI3 (mole ratio 1/4/3 [76]; 1/(2.2 to 3)/(2.2 to 3) [2, p. 107], [3, 4, 8, 14, 24, 29, 30], [35, p. 143], [37, 58]; 1/(2 to 2.5)/(2 to 5) [1 0]; 1/2.8/0.25 [12, 33]) in CH 2CI2 with areactiontime of ~ 2 hat the boiling point [3, 4, 10, 14, 76], 30 to 35°C [30], or (better) room temperature [2
