Summary
A novel reaction of 11,11,12,12-tetracyanoanthraquinodimethane — its transformation into 10-dicyanomethylene-anthrone hydrazone by reaction with hydrazine — is reported. This hydrazone seems to be a convenient starting material in the synthesis of anthracene derivatives and compounds incorporating anthracenic fragments, but is itself as a conjugated donor acceptor system a material with interesting physical properties.
Zusammenfassung
Eine neue Reaktion von 11,11,12,12-Tetracyanoanthrachinodimethan — seine Umsetzung zum 10-Dicyanomethylen-anthronhydrazon durch Reaktion mit Hydrazin — wird beschrieben. Dieses Hydrazon könnte als Ausgangsmaterial für die Synthese von Anthracenderivaten dienen, zeigt aber auch selbst als konjugiertes Donor-Akzeptorsystem interessante physikalische Eigenschaften.
References
Aumüller A., Hünig S. (1984) Ann. Chem.1984: 618
Kini A. M., Cowan D. O., Gerson F., Möckel R. (1985) J. Am. Chem. Soc.107: 556
Yamaguchi S., Tatemitsu H., Sakata Y., Misumi S. (1983) Chem. Lett.193: 1229
Schubert U., Aumüller A., Hünig S. (1985) Ann. Chem.1985: 1216
Heimer N. E., Mattern D. L. (1993) J. Am. Chem. Soc.115: 2217
Falk H., Oberreiter M. (in press) Monatsh. Chem.
Hertler W. R., Hartzler H. D., Acker D. S., Benson R. E. (1962) J. Am. Chem. Soc.84: 3387
PCMODEL. Serena Software 1990
Paley M. S., Harris J. M., Looser H., Baumert J. C., Jundt D., Twieg R. J. (1989) J. Org. Chem.54: 3774; for an application of this valuable method to linear oligopyrroles see: Falk H., Hemmer D. (1992) Monatsh. Chem.123: 779
Ong B. S., Keoshkerian B. (1984) J. Org. Chem.49: 5002
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Falk, H., Vaisburg, A.F. A novel reaction of 11,11,12,12-tetracyanoanthraquinodimethane: The formation of 10-dicyanomethylene-anthrone hydrazone. Monatsh Chem 125, 549–551 (1994). https://doi.org/10.1007/BF00811847
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00811847