Electrochemically induced aromatic nucleophilic substitution in p-diiodobenzene with [( η5-C 5H 5)Fe(CO) 2] − and [( η5-C 5H 5)W(CO) 3] −-anions

• Published in: Journal of organometallic chemistry Vol. 487; no. 1; pp. 163 - 166
• Main Authors: Magdesieva, T.V., Kukhareva, I.I., Artamkina, G.A., Beletskaya, I.P., Butin, K.P.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 08-02-1995
• Subjects: Bond activation; Electrochemistry; Iron; Tungsten; Electrochemistry; Iron; Bond activation; Tungsten
• DOI: 10.1016/0022-328X(94)05077-O
• EISSN: 1872-8561
• ISSN: 0022-328X

The reactions of
p-diiodobenzene with [(
η
5-C
5H
5)Fe(CO)
2]
− and [(
η
5-C
5H
5W(CO)
3]
− were studied using a complex of electrochemical techniques (cyclic voltammetry, rotating ring-disk electrode and preparative scale electrolysis). For [(
η
5-C
5H
5)Fe(CO)
2]
− it was shown that aromatic nucleophilic substitution of either one or two iodine atoms in
p-diiodobenzene for
η
5-cyclopentadienylirondicarbonyl can be performed through electrochemical activation of the aryl halide. The ratio of (
η
5-C
5H
5)Fe(CO)
2C
6H
4I and (
η
5-C
5H
5)Fe(CO)
2C
6H
4Fe(CO)
2(
η
5-C
5H
5) was shown to depend strongly on the electrolysis conditions: electrode potential electrolysis duration, etc. The yield of (
η
5-C
5H
5)Fe(CO)
2C
6H
4Fe(CO)
2(
η
5-C
5H
5) can be considerably increased when (
η
5-C
5H
5)Fe(CO)
2C
6H
4I is taken as a starting compound. For [(
η
5-C
5H
5)W(CO)
3I
− the main product of the reaction with
p-diiodobenzene is (
η
5-C
5H
5)W(CO)
3I.