アルキリデンシクロプロパノンアセタールのビニル求核置換-環開裂反応

藤原 康次; 毛利 洋; 風神 豊; 藤田 守文; 奥山 格

doi:10.11494/kisoyuki.53.0.37.0

53rd Symposium on Organic Reactions

Session ID : P-13

DOI https://doi.org/10.11494/kisoyuki.53.0.37.0

Conference information

Co-host: The Chemical Society of Japan, The Chemical Society of Japan, Kyushu Branch, The Society of Synthetic Organic Chemistry, Japan (Cooperation)

Nucleophilic Vinylic Substitution of Alkylidenecyclopropanone Acetals

*Koji Fujiwara, Hiroshi Mouri, Yutaka Kazekami, Morifumi Fujita, Tadashi Okuyama

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Keywords: Alkylidenecyclopropanone, Silylacetal, Cyclopropane, Vinylic Substitution, Lewis Acid

CONFERENCE PROCEEDINGS FREE ACCESS

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Abstract

Alkylidenecyclopropanone silylacetals undergo the ring-opening reaction under acidic conditions. The vinylic bond was cleaved to give nucleophilic substitution products via allylic cation intermediate. When the silyl acetal was treated with fluorid ion, allylic bond cleavege occured via carbanion intermediate.

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