Naphtho(2,3-c)furan-1,3-dione → 5,12-Naphthacenedione

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Reaction Steps

Substituted tetracenes also can be prepared by any known method, including for example, the following sequence of reactions: 1) the condensation of naphthalene-2,3-dicarboxylic anhydride and benzene derivatives, 2) dehydration to form the corresponding tetracene-5,12-quinone, 3) and reduction of the quinone to give the corresponding tetracene derivative. Such methods are taught, e.g., in Waldmann, H. and Mathiowetz, H., Ber. dtsch. Chem. Ges. 64, 1713 (1931), Weizmann, C., Haskelberg, L. and Berlin, T., J. Chem. Soc. 398 (1939); Waldemann, H. and Plak, G., J. prakt. Chem. (2) 150, 113, 121 (1938), which are herein incorporated by reference. Other examples of synthesis of alkyl homologues of tetracene include: 2-methyltetracene (Coulson, E. A., J. Chem. Soc. 1406 (1934)), 5-methyltetracene (Clar, E. and Wright, J. W., Nature, Lond. 63, 921 (1949)), 2-isopropyltetracene (Cook, J. W., J. Chem. Soc. 1412 (1934)), 1,6-dimethyltetracene (Fieser, L. F. and Hershberg, E. B. J. Amer. Chem. Soc. 62, 49 (1940)), 2,8-dimethyltetracene (Fieser, L. F. and Hershberg, E. B. J. Amer. Chem. Soc. 62, 49 (1940) and Coulson, E. A., J. Chem. Soc. 1406 (1934)), 2,9-dimethyltetracene (Coulson, E. A., J. Chem. Soc. 1406 (1934)), and 5,12-dimethyltetracene (Wolf, J., J. Chem. Soc. 75, 2673 (1953)), which are herein incorporated by reference.

Provenance & Evidence