Novel synthesis of the mesoionic system 1,3-oxazolium-4-olate
Novel synthesis of the mesoionic system 1,3-oxazolium-4-olate
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介离子体系1,3-恶唑鎓-4-油酸盐的新合成
DOI：
10.1021/jo00343a024
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发表时间：
1982
影响因子：
3.6
通讯作者：
J. Freeman
中科院分区：
文献类型：
--
作者：
M. Haddadin;Asma M. Kattan;J. Freeman
在撰写一篇关于恶氮杂环类化合物的综述的过程中，1我们观察到一个显著的例外，即IV-芳基硝酮和芳香族N-氧化物分别光解重排为酰胺和内酰胺。有人声称，N-苯基二苯甲酰硝酮(1)通过光化学重排得到“JV-苯基二苯甲酰氮杂环丙烷”(2)。2后来，其他人报道了3在对二甲苯回流温度下从1热得到相同的化合物。此外，有人声称，恶氮杂环丁2“在惰性气氛中加热到250℃后可以原封不动地恢复到原来的温度”。进行了进一步的化学转化，并将产物指定为方案I所示的结构。
During the process of writing a review on oxaziridines, 1 we observed a report of a remarkable exception to the general photolytic rearrangement of IV-arylnitrones and aromatic N-oxides to amides and lactams, respectively. It was claimed that N-phenyldibenzoylnitrone (1) rearranged photochemically to give “JV-phenyldibenzoyloxazirine”(2) in essentially quantitative yield. 2 Later, others reported3 the same compound was obtained thermally from 1 at the reflux temperature of p-xylene. Moreover, it was claimed that oxaziridine 2 “can be recovered unchanged after heating to 250 C in an inert atmosphere”. Further chemical transformations were carried out and the products were assigned the structures shown in Scheme I.