Radical intermediates in photosubstitution reactions of anthraquinones
Radical intermediates in photosubstitution reactions of anthraquinones
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蒽醌光取代反应中的自由基中间体
DOI：
10.1021/ja00792a074
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发表时间：
1973
影响因子：
15
通讯作者：
L. Herwaldt
中科院分区：
文献类型：
--
作者：
G. G. Wubbels;D. Tollefsen;Robert S. Meredith;L. Herwaldt
最近，人们对合成取代环丁酮的方法产生了相当大的兴趣。1这些方法都不涉及环丁酮本身的取代。2我们发现由环丁酮二烯丙基缩酮(2)可以方便地合成2-烯丙基环丁酮(I)。3以环丁酮和烯丙醇为原料，在2，2-二甲氧基丙烷和甲苯磺酸存在下，以93%的产率合成了缩酮2，BP81-82(15.5mM)，26D 1.4445，6。在TSA存在下，2在185℃加热，得到1，BP 89-90(72 Mm)，×26D 1.4476，定量产量。迄今未知的官能团取代的环丁酮1提供了一种潜在的来源，如下面列举的那样。从2的相应类似物成功地制备了环丁酮3和4，证明了2对1反应的潜在的一般性。
Recently there has been considerable interest in methods for the synthesis of «-substituted cyclobuta-nones. 1 None of these methods involves substitution of cyclobutanone itself. 2 Wehave found that 2-allyl-cyclobutanone (I) can be conveniently prepared from cyclobutanone diallyl ketal (2). 3 The ketal 2, bp 81-82 (15.5 mm),«26d 1.4445, 6 was prepared in 93% yield from cyclobutanone and allyl alcohol in the pres-ence of 2, 2-dimethoxypropane and toluene sulfonic acid (TSA). Heating of 2 at 185 in the presence of TSA gave 1, bp 89-90 (72 mm),«26d 1.4476, in quan-titative yield. The hitherto unknown, functionally substituted cyclobutanone 1 provides a potential source of a variety of «-substituted cyclobutanones, as illus-trated below. The potential generality of the reaction of 2 togive 1 has been demonstrated by the successful preparation of the cyclobutanones 3 and 4 from the corresponding analogs of 2.