Favorskii-type rearrangement of .ALPHA.,.ALPHA.'-dihalo ketones with sodiomalonates leading to conjugated enone derivatives.
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概要
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A new synthetic method of conjugated enones by the use of carbanion-induced Favorskii-type rearrangement is described. The reaction of α,α′-dihalo ketones R<SUP>1</SUP>R<SUP>2</SUP>(X)CC(O)CH<SUB>2</SUB>X with sodiomalonates Na<SUP>+</SUP> <SUP>−</SUP>CR<SUP>3</SUP>(CO<SUB>2</SUB>R<SUP>4</SUP>)<SUB>2</SUB> in THF at 0°C—room temperature gave conjugated enones R<SUP>1</SUP>R<SUP>2</SUP>C=CHC(O)CR<SUP>3</SUP>(CO<SUB>2</SUB>R<SUP>4</SUP>)<SUB>2</SUB> in 42–66% yields. The reaction can be also adaptable to the enolates of ethyl cyanoacetate or malononitrile to give the corresponding enones.
- 公益社団法人 日本化学会の論文
著者
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Sakai Takashi
Department Of Applied Chemistry Faculty Of Engineering Okayama University
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Utaka Masanori
Department Of Applied Chemistry Faculty Of Engineering Okayama University
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Ishikawa Mutsumi
Department of Synthetic Chemistry, School of Engineering, Okayama University
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Amano Eiichiro
Department of Synthetic Chemistry, School of Engineering, Okayama University
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Takeda Akira
Department of Applied Chemistry, Faculty of Engineering, Okayama University
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