Interaction of aryloxychlorocarbenes with acetylenedicarboxylate: novel formation of polyfunctional butadienes and 8-oxatricyclo[3.2.1.0(2.4)]oct-6-enes.
The interaction of aryloxychlorocarbenes with dialkyl acetylenedicarboxylates has been examined. Thermolyses of 3-aryloxy-3-chlorodiazirines in the presence of acetylenedicarboxylate resulted in the formation of unexpected polyfunctional 1,3-butadienes and 8-oxatricyclo[3.2.1.0(2.4)]oct-6-enes or of 2-aryoxycarbonylmaleates dependent upon reaction conditions. This work confirmed the nucleophilicity of aryloxychlorocarbenes and underlined their synthetic potential.
Cheng
Ying
Y
Chemistry Department, Beijing Normal University, Beijing 100875, China. ycheng2@bnu.edu.cn
Zhu
Qing
Q
Li
Quan Song
QS
Meth-Cohn
Otto
O