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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.