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The unique nucleophilic reactivity of arylaminochlorocarbenes
Ying Cheng1, Hua Yang, Otto Meth-Cohn
1Department of Chemistry, Beijing Normal University, Beijing 100875, China. yincheng@95777.com
Chemical Communications (Cambridge, England)
|March 4, 2003
Abstract:
4-Methyl and 4-methoxyphenylaminochlorocarbene (readily formed by deprotonation of the Vilsmeier reagent derived from the corresponding N-methylformanilide with Hünig's base) reacted with diethyl acetylenedicarboxylate to give 1:2 quinoline adducts, while p-halophenylaminochlorocarbenes yielded benzoazepine derivatives from 2:1 interaction of the carbene with oxalyl chloride under the same reaction conditions.