Lewis Acid Mediated Synthesis of 2-Alkenenitriles Using <i>C</i>,<i>N</i>-Bis(trimethylsilyl)ketenimine and Carbonyl Compounds

• Isamu Matsuda

  Department of Synthetic Chemistry, Faculty of Engineering, Nagoya University

• Hisashi Okada

  Department of Synthetic Chemistry, Faculty of Engineering, Nagoya University

• Yusuke Izumi

  Department of Synthetic Chemistry, Faculty of Engineering, Nagoya University

抄録

2-Substituted 2-alkenenitriles are obtained in the condensation reaction of carbonyl compounds with C,N-bis(trimethylsilyl)ketenimine in the presence of Lewis acid. The combination of tris(trimethylsilyl)ketenimine and aldehydes results in the high E-selective formation of 2-trimethylsilyl-2-alkenenitriles. Among some Lewis acids, magnesium bromide gives the best E-selectivity in the formation of 2-trimethylsilyl-2-undecenenitrile. Stereospecific protodesilylation of 2-trimethylsilyl-2-alkenenitriles in an aqueous methanol solution of potassium fluoride accomplishes a new route to (Z)-2-alkenenitriles from aldehydes.

収録刊行物

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 56 (2), 528-532, 1983-02-01

  Oxford University Press (OUP)

キーワード

• General Chemistry

詳細情報

• CRID: 1360846644032228992
• NII論文ID: 130001985630
• DOI: 10.1246/bcsj.56.528
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/56/2/528/55667685/bcsj.56.528.pdf
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