Benzodioxole Chemistry. 5. Dramatic Substituent Effect in the Reaction of Carbonyl-bridged Cyclic Carbonates with Methoxide Ion
Benzodioxole Chemistry. 5. Dramatic Substituent Effect in the Reaction of Carbonyl-bridged Cyclic Carbonates with Methoxide Ion
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苯并间二氧杂环戊烯化学。
DOI：
10.3987/com-03-9911
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发表时间：
2004
期刊：
影响因子：
0.6
通讯作者：
W. S. Grove
中科院分区：
文献类型：
--
作者：
E. A. Harrison;W. S. Grove
在室温下，苯并二氧二酮（2c-e）在k2co3 /MeOH中高产率转化为环戊酮（3c-e），而类似物（2a）和（2b）在此条件下只生成环己二烯羧酸酯（la和1b）。在5-10℃2c与k2co3 /MeOH反应中分离到中间产物6(R，R'=Me R'= Ph)，表明3是由OMe（-）攻击2的酯羰基引发的。
Benzodioxolediones (2c-e) undergo high-yield conversion to cyclopentenones (3c-e) in K 2 CO 3 /MeOH at room temperature, while analogs (2a) and (2b) yield exclusively cyclohexadiene carboxylates (la and 1b) under these conditions. Isolation of intermediate 6(R,R'=Me R"=Ph) from the reaction of 2c with K 2 CO 3 /MeOH at 5-10°C suggests that 3 is formed in a process triggered by attack of OMe ( - ) at the ester carbonyl of 2.