New Methods and Reagents in Organic Synthesis. 17. Trimethylsilydiazomethane (TMSCHN_2) as a Stable and Safe Substitute for Hazardous Diazomethane. Its Application to the Arndt-Eistert Synthesis
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概要
- 論文の詳細を見る
Although diazomethane is used in the Arndt-Eistert synthesis, it is both highly toxic and also explosive, and hence should be very carefully handled. In place of this hazardous diazomethane, stable and safe trimethylsilyldiazomethane (TMSCHN_2) was found to be very useful for the Arndt-Eistert synthesis. TMSCHN_2 was easily acylated with a carboxylic acid chloride in tetrahydrofuran-acetonitrile, and thermal treatment of the acylated product in benzyl alcohol and 2,4,6-trimethylpyridine smoothly gave the benzyl ester of a homologated acid. Nucleophiles other than benzyl alcohol could also be used. TMSCHN_2 may also be able to replace diazomethane in other areas of chemistry.
- 公益社団法人日本薬学会の論文
- 1981-11-25
著者
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塩入 孝之
名城大学薬学部
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塩入 孝之
Faculty Of Pharmaceutical Sciences Nagoya City University
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青山 豊彦
名古屋市立大学大学院薬学研究科
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青山 豊彦
Faculty Of Pharmaceutical Sciences Nagoya City University
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