BETA-CYANOCYCLOBUTENONE AS A HIGHLY REACTIVE DIENOPHILE IN COMPARISON TO BETA-CYANOCYCLOPENTENONE
BETA-CYANOCYCLOBUTENONE AS A HIGHLY REACTIVE DIENOPHILE IN COMPARISON TO BETA-CYANOCYCLOPENTENONE
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DOI：
10.1016/s0040-4020(01)91012-9
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发表时间：
1991-09-16
期刊：
影响因子：
2.1
通讯作者：
SUSTMANN, R
中科院分区：
文献类型：
--
作者：
BIENFAIT, B;COPPEMOTTE, G;SUSTMANN, R
α-氯丙烯腈与丙二烯的热[2+2]环加成，然后臭氧分解，然后消除HCl，即可得到新的β-氰基环丁烯酮1(方案1)。1在室温下很容易发生Diels-Alder反应。1在[4+2]环加成反应中的高活性与同系物氰环戊酮9的低反应活性形成强烈对比(方案4)。这与计算(PM3方法)是一致的。
The thermal [2+2] cycloaddition of alpha-chloroacrylonitrile to allene followed by ozonolysis, then elimination of HCl provides access to the new beta-cyanocyclobutenone 1 (Scheme 1). Diels-Alder reactions of 1 occur very easily at room temperature. The high reactivity of 1 in [4+2] cycloadditions strongly contrasts with the low reactivity of the homologous cyanocyclopentenone 9 (Scheme 4). This is in agreement with calculations (PM3 method).