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The reductive metalation of 9‐phenylacridine
Author(s) -
Smith James G.,
Fogg Deryn E.
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220355
Subject(s) - chemistry , metalation , medicinal chemistry , ethyl chloroformate , electrophile , methanol , ring (chemistry) , chloroformate , sodium methoxide , organic chemistry , catalysis
The reductive metalation of 9‐phenylacridine by sodium to a dianion is described and the reactions of the dianion with electrophiles investigated. Reactions of the dianion with methanol, dimethyl sulfate, X(CH 2 ) n X (n = 2,3,4, X = Cl, Br), and methyl chloroformate were studied. Reactions occurred exclusively at the 9 and 10 positions forming 9,10‐dihydro‐9‐phenylacridine derivatives. Of particular interest was the fact that the dianion was dialkylated with 1,2‐dichloroethane but monoalkylated at the 9‐position with 1,3‐dichloropropane and 1,4‐dichlorobutane. These results are compared to those obtained with dianions derived from other heterocyclic systems and analyzed using Baldwin's Rules for Ring Closure.