Trimethylsilylketene. Cycloadditions of ketenes and aldehydes
Trimethylsilylketene. Cycloadditions of ketenes and aldehydes
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三甲基甲硅烷基乙烯酮。
DOI：
10.1021/jo01319a015
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发表时间：
1979
期刊：
影响因子：
--
通讯作者：
K. Saidi
中科院分区：
文献类型：
--
作者：
W. T. Brady;K. Saidi
BF_3-E_20导致顺式和铁-2-氧杂环丁酮的形成。在BFa-EtaO存在下，三甲基硅基烯酮与α，β-不饱和醛、肉桂醛、巴豆醛、糠醛和β-甲基肉桂醛反应，生成三甲基硅基二烯酸酯。这些酯衍生自2-氧杂环丁酮，其经历了伴随开环反应的硅从碳到氧的迁移。二氯乙烯酮和二苯基乙烯酮与肉桂醛反应生成相应的2-氧杂环丁烷酮，2-氧杂环丁烷酮容易脱羧生成取代的1，3-丁二烯。
BF3-EÍ20 resulted in the formation of the cis-and irons-2-oxetanones. Trimethylsilylketene reacted with a, fJ-unsaturated aldehydes, cinnamaldehyde, crotonaldehyde, furfural, and-methylcinnamaldehyde, in the presence of BFa-EtaO, to yield trimethylsilyl dienoate esters. These esters are derived from the 2-oxetanones which under-went a silicon migration from carbon to oxygen accompanied by a ring-opening reaction. Dichloroketene and di-phenylketene reacted with cinnamaldehyde to yield the corresponding 2-oxetanones, which readily decarboxylated to the substituted 1, 3-butadienes.