SYNTHESIS OF CYCLOBUTENONE
SYNTHESIS OF CYCLOBUTENONE
复制标题
DOI：
10.1021/ja00739a020
复制
发表时间：
1971-01-01
影响因子：
15
通讯作者：
SIEJA, JB
中科院分区：
文献类型：
--
作者：
SIEJA, JB
以3-溴环丁酮和3-氯环丁酮为原料，分别由异烯和烯酮经独立的路线合成环丁酮。迄今为止，环丁烯酮(5)尚未被分离出来，尽管已报道了许多取代环丁烯酮的例子。我们希望报道5的合成和分离，它是通过两个独立的途径得到的，都收敛到3-卤代环丁酮作为直接前体。3-Bromocyclobutanone。首先按方案一制备环丁酮，化合物1、2、3按文献方法制备。前驱体是通过对Hunsdiecker反应进行修饰而制备的。通过光谱和元素分析证实了4的结构（见实验部分）。方案一的一个限制是2到3的转化，因为粗3是一种黑色的，水溶固体，难以纯化。在小范围内臭氧溶解2可能更可取。
Cyclobutenone was prepared from 3-bromo-and3-chlorocyclobutanone, which were synthesized by independent routes from aliene and ketene, respectively.Cyclobutenone (5) has thus far escaped isolation, 1 al-though numerous examples of substituted cyclo-butenones have been reported. We wish to report the synthesis and isolation of 5, which was obtained by two independent routes, both converging to a 3-halocyclobutanone as the immediate precursor. 3-Bromocyclobutanone. Cyclobutenone was first prepared as shown in Scheme I. Compounds 1, 2, and 3 were prepared according to literature methods. 2· 3 The precursor 4 was prepared by a modification4 of the Hunsdiecker reaction. The structure of 4 was proved by spectral and elemental analyses (see Experimental Section). A limitation of Scheme I is the conversion of 2 to 3, because crude 3 is obtained as a black, water-sol-uble solid which is difficult to purify. Ozonolysis of 2 would probably be preferable on a small scale.