Organic compounds -- part of the class 532-570 series – Organic compounds – Heavy metal containing
Patent
1990-12-12
1992-05-05
Prescott, Arthur C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heavy metal containing
556138, 556140, 556144, C07F 1702
Patent
active
051109646
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for producing ferrocenoyl derivatives, more particularly it is concerned with a process for an efficient production of ferrocenoyl derivatives by reacting a ferrocene derivative with a monocarboxylic acid or a dicarboxylic acid in the presence of a catalyst.
BACKGROUND ART
Generally, ferrocenoyl derivatives are very useful as the intermediate material for producing highly active functional materials having a ferrocene skeleton, such as functional polymers, LB films, surfactants, charge-transfer complexes, ion sensors, masking reagents, and coupling agents.
Such ferrocenoyl derivatives have heretofore been produced according to a process in which a carboxylic acid is converted into acid halide and then the resulting acid halide is reacted with a ferrocene derivative in the presence of a Lewis acid catalyst such as aluminum chloride.
That process, however, will involve byproducts in which each of two five-membered rings of ferrocene derivatives has been acylated. Accordingly, to inhibit such byproducts, the way of adding ferrocene derivatives must be selected. Moreover, when a compound containing halogen atom is used as the carboxylic acid, the reaction temperature should be controlled to be under 5.degree. C., so as to inhibit dehalogenation reaction.
Further, the acylation reaction of ferrocene derivative with the use of catalysts such as polyphosphoric acid has been known (J. Am. Chem. Soc. 79,3290 (1957)). It is, however, an intramolecular reaction, and any intermolecular acylation of ferrocene derivatives which is required for selectivity has not been known.
Particularly, to produce a ferrocenoyl derivative having carboxyl group, a very complicated process has been required wherein one carboxylic acid of dicarboxylic acid is esterified by use of disproportionation reaction, then the other unreacted carboxylic acid is acid-halogenated, and the resulting product is reacted with ferrocene derivative under the condition of usual Friedel-Crafts reaction, to obtain ferrocenoyl derivative carboxylate, and after that, said ester is hydrolyzed (PCT Int. Appln. Laid-Open WO89/01939).
Above process, however, required so many steps and complicated operations but the yield was insufficient that it was not suitable for practical use.
DISCLOSURE OF INVENTION
Under these circumstances, the present inventors had earnestly repeated investigations to overcome the above defects of the conventional process described above, and to produce ferrocenoyl derivatives efficiently with simple steps.
As the result, it was found that the object can be attained by reacting directly a ferrocene derivative with monocarboxylic acid or dicarboxylic acid in the presence of a catalyst comprising phosphoric acid or its derivative. The present invention has been accomplished based on such findings.
The present invention provides a process for producing ferrocenoyl derivatives which is characterized by reacting a ferrocene derivative with a monocarboxylic acid or a dicarboxylic acid in the presence of a catalyst .
BRIEF DESCRIPTION OF DRAWINGS
FIG. 1 to FIG. 16 show each .sup.1 H--NMR (proton nuclear magnetic resonance) spectrum of the ferrocenoyl derivative produced in Examples 1 to 16, respectively.
THE MOST PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION
The present invention employs, as the reaction material, ferrocene derivative and monocarboxylic acid or dicarboxylic acid. Herein, as the ferrocene derivative, ferrocene and various substitution products thereof in a wide range are used. Said substituted ferrocenes are not critical, and include various ones in which various substituent groups may have been introduced into the ferrocene skeleton.
Said substituents of ferrocene may vary as long as they do not inhibit the proceeding of ordinary Friedel-Crafts reaction, and the positions and the numbers of said substituents are not specified as long as Friedel-Crafts reaction is not inhibited in proceeding. Preferred ferrocene derivatives are those represented by the gener
REFERENCES:
patent: 3960911 (1976-06-01), Suschitzky et al.
patent: 3989731 (1976-11-01), Talbot
patent: 5041582 (1991-08-01), Eida et al.
Herve' des Abbayes & Rene' Dabard, Ste're'o-chimie dans 1 a Se'rie des ferrocenyl-cyclohe'xenones .alpha. et .beta. disubstitue'es, Compt. Rend. Acad. Sci. t. 276, Jun. 1973, Ser. C, pp. 1763 to 1766.
Hiroi Yoshio
Yokoyama Seiichiro
Idemitsu Kosan Co. Ltd.
Prescott Arthur C.
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