Abstract
TheDiels-Alder adduct2 from pyrene and hexachlorocyclopentadiene exhibits a different substitution pattern than pyrene itself, namely that of phenanthrene. By reactions with the adduct following Retro-Diels-Alder splitting, pyrene substitution products are accessible that cannot be obtained by direct substitution of pyrene. This is demonstrated by the synthesis of 4-chloropyrene (5) and 4-bromopyrene (6).
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Literatur
A. Streitwieser, Molecular Orbital Theory for Organic Chemists, S. 336. New York-London: J. Wiley. 1961.
E. Clar, Polycyclic Hydrocarbons, Bd. 2, S. 119. London-New York: Academic Press. 1964.
M. Zander, Erdöl und Kohle-Erdgas-Petrochemie15, 362 (1962).
C. Jutz, R. Kirchlechner undH. J. Seidel, Chem. Ber.102, 2301 (1969);R. Bolton, J. Chem. Soc.1964, 4637;H. Vollmann, H. Becker, M. Corell undH. Streeck, Ann. Chem.531, 1 (1937);G. Förster undJ. Wagner, Z. Phys. Chem.B37, 353 (1937).
A. Streitwieser, jr., R. G. Lawler undD. Schwaab, J. Org. Chem.30, 1470 (1965).
K. F. Lang undM. Zander, Chem. Ber.97, 218 (1964).
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Herrn Prof. Dr.Oskar E. Polansky zum 60. Geburtstag gewidmet.
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Blümer, GP., Zander, M. Synthese und Reaktionen desDiels-Alder-Addukts aus Pyren und Hexachlorcyclopentadien. Monatshefte für Chemie 110, 1233–1236 (1979). https://doi.org/10.1007/BF00910971
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DOI: https://doi.org/10.1007/BF00910971