1,1-Ethylene-1H-azulenium ion and its alkyl substituted derivatives: Synthesis, characterization, and some reactions thereof

Mitsunori Oda*, Takanori Kajioka, Takuya Uchiyama, Kohki Nagara, Tetsuo Okujima, Shunji Ito, Noboru Morita, Toshio Sato, Ryuta Miyatake, Shigeyasu Kuroda

*この論文の責任著者

研究成果: ジャーナルへの寄稿学術論文査読

11 被引用数 (Scopus)

抄録

1,1-Ethylene-1H-azulenium tetrafluoroborate (1b) and its alkyl substituted derivatives, 6-t-butyl (1c) and 4-isopropyl-3,8-dimethyl ones (Id), were synthesized starting from their corresponding azulenes by a three- step sequence which includes reduction, cyclopropanation and hydride abstraction reactions. The cation 1b and its 6-t-butyl derivative 1c, generated in deuterated acetonitrile at -20 °C, were characterized by low- temperature NMR spectroscopy. On the other hand, the cation Id was isolated os slightly unstable, greenish-yellow crystals. While the cation 1b in solution underwent expansion of the cyclopropane ring at elevated temperatures, 1c and 1d just decomposed. All the cations were found to react easily with nucleophiles to give thermodynamically controlled, stable addition products at their cyclopropane methylene carbons.

本文言語英語
ページ(範囲)6081-6096
ページ数16
ジャーナルTetrahedron
55
19
DOI
出版ステータス出版済み - 1999/05/07

ASJC Scopus 主題領域

  • 生化学
  • 創薬
  • 有機化学

フィンガープリント

「1,1-Ethylene-1H-azulenium ion and its alkyl substituted derivatives: Synthesis, characterization, and some reactions thereof」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル