CYCLOADDITIONS OF KETENES WITH N-FLUORENYLIDENEALKYL AMINE AND N-FLUORENYLIDENEALKYL ARYLAMINE OXIDES - SYNTHESIS OF SPIROOXAZOLIDINONES AND SPIROISOXAZOLIDINONES
CYCLOADDITIONS OF KETENES WITH N-FLUORENYLIDENEALKYL AMINE AND N-FLUORENYLIDENEALKYL ARYLAMINE OXIDES - SYNTHESIS OF SPIROOXAZOLIDINONES AND SPIROISOXAZOLIDINONES
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DOI：
10.1021/jo01331a002
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发表时间：
1979-01-01
影响因子：
3.6
通讯作者：
JOULLIE, MM
中科院分区：
文献类型：
--
作者：
ABOUGHARBIA, MA;JOULLIE, MM
研究了几种IV-亚甲基胺和-烷基胺氧化物(1和2)与环戊亚甲基乙烯酮、叔丁基甲氧基乙酮和异丁基环丙酮酮的环加成反应。总体而言，IV-芳基衍生物得到螺恶唑烷酮(3)，而N-烷基衍生物得到螺异恶唑烷酮(4)。3和4的~1H和~(13)C核磁共振研究证实了它们的结构。提出了一种解释所有观察到的环加成产物的机理方案。
The cycloadditions of several IV-fluorenylidenearylamine and-alkylamine oxides (1 and 2) with cyclopentamethyleneketene, tert-butylcarbethoxyketene, and ieri-butylcycanoketene were investigated. In general, the IV-aryl derivatives afforded spirooxazolidinones (3) while the N-alkyl derivatives gave spiroisoxazolidinones (4). 1H NMR and 13C NMR studies of 3 and 4 were carried out to substantiate their structures. A mechanistic scheme which accounts for all of the observed cycloaddition products is proposed.