1,4‐Addition von Kalium‐cycloheptatrienid an (9‐Phenyl‐)Anthracen | Zendy

Kaupp Gerd | Zendy; Grüter HeinzWilli | Zendy; Teufel Eberhard | Zendy

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1,4‐Addition von Kalium‐cycloheptatrienid an (9‐Phenyl‐)Anthracen

Author(s) -

Kaupp Gerd,

Grüter HeinzWilli,

Teufel Eberhard

Publication year - 1982

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19821150924

Subject(s) - chemistry , anthracene , adduct , cycloheptatriene , medicinal chemistry , potassium , nuclear magnetic resonance spectroscopy , liquid ammonia , ion , ammonia , stereochemistry , organic chemistry

1,4‐Addition of Potassium Cycloheptatrienide to ( 9 ‐Phenyl‐)Anthracene In liquid ammonia the cycloheptatriene anion adds to anthracene ( 3 ) and 9‐phenylanthracene ( 9 ) to give the anions 4 and 10 , resp., which are quenched at −35°C to give the substitutive 1,4‐adducts 5 and 11 + 12 , resp. Upon heating up to 20°C the intermediate anion 4 cyclizes to the Diels‐Alder product 6 , which is quenched to give the asymmetric and symmetric [4 + 2]‐adducts 7 and 8 . The structures of the products have been established primarily by high‐field 1 H‐NMR spectroscopy.

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